Alantoina

SciFinder® Page 1
12. Single Step
Step Stages Notes Yield

1 1.1 C:H2NSO3H, 6 h, 75°C optimization study, optimized on
temperature and reaction time and
stoichiometry, Reactants: 2, Catalysts:
1, Steps: 1, Stages: 1
Transformation:
Uncategorized
Source
Synthesis of allantoin catalyzed by
sulfamic acid
Liu, Li-xiu; He, Ai-jiang; Li, Xiang-biao
Huagong Jishu Yu Kaifa
Volume 41
Issue 11
Pages 18-20
Journal
2012
Company/Organization
Yibin Vocational and Technical
College
Yibin, Peop. Rep. China 644003
Number of Steps
1
CASREACT ®: Copyright © 2017 American Chemical Society. All Rights Reserved. CASREACT contains reactions
from CAS and from: ZIC/VINITI database (1974-1999) provided by InfoChem; INPI data prior to 1986; Biotransformations
database compiled under the direction of Professor Dr. Klaus Kieslich; organic reactions, portions copyright 1996-2006
John Wiley & Sons, Ltd., John Wiley and Sons, Inc., Organic Reactions Inc., and Organic Syntheses Inc. Reproduced
under license. All Rights Reserved.
13. 2 Steps

SciFinder® Page 2
1 optimization study, optimized on
1.1 R:H2SO4, R:O2, R:AlCl3, C:NaNO2, S:H2O, 3 76%
stoichiometry, temperature, time,
h, 25°C reactant amount, Reactants: 1,
Reagents: 3, Catalysts: 1, Solvents: 1,
Steps: 1, Stages: 1
[Reactant]

2 2.1 3 h, 75°C optimization study, optimized on 61%
Reactants: 2, Steps: 1, Stages: 1
Source
Preparation of allantoin from glyoxal
by atmospheric oxygen oxidation with
sulfuric acid as a medium
Wang, Xiaobing; Guo, Wali; Li, Ping;
Deng, Xinzhong; Dai, Xi; Zhu, Hong;
Li, Lei; Shan, Yi
Jingxi Shiyou Huagong
Volume 30
Issue 1
Pages 67-70
Journal
2013
College of Chemical Engineering
Shenyang University of Chemical
Technology
Shenyang, Liaoning Province, Peop.
Rep. China 110142
Number of Steps
2
14. Single Step
SciFinder® Page 3

1 1.1 3 h, 75°C optimization study, optimized on 61%
Transformation:
1. Formation of N/O/S Heterocycles
Source
Preparation of allantoin from glyoxal
by atmospheric oxygen oxidation with
sulfuric acid as a medium
Wang, Xiaobing; Guo, Wali; Li, Ping;
Deng, Xinzhong; Dai, Xi; Zhu, Hong;
Li, Lei; Shan, Yi
Jingxi Shiyou Huagong
Volume 30
Issue 1
Pages 67-70
Journal
2013
Technology
Shenyang, Liaoning Province, Peop.
Rep. China 110142
Number of Steps
1
15. Single Step
SciFinder® Page 4

1 1.1 C:7803-63-6, C:H2SO4, S:H2O, rt → 68°C; 12 optimization study, Reactants: 2,
h, 68°C 80%
Catalysts: 2, Solvents: 1, Steps: 1,
Stages: 1
Transformation:
Source
Method for synthesis of allantoin
Hu, Wenjing; Cai, Mengmeng
Assignee Beijing Sunpu Biochemical
and Technology Co., Ltd., Peop. Rep.
China
2013
Patent Information
Jan 30, 2013
CN 102898376
A
Number of Steps
1
16. 3 Steps

1 Reactants: 1, Reagents: 1, Steps: 1,
1.1 R:D2O Stages: 1
[Reactant]

SciFinder® Page 5
2 2.1 S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, 5°C photochemical, sealed and
thermostated glass reactor used,
mercury vapor discharge lamp used,
global time of 3 weeks with initial 72h
UV irradiation, Reactants: 2, Solvents:
SciFinder® Page 6
Additional Product(s):
SciFinder® Page 7
SciFinder® Page 8
Reaction Protocol
Step 2
Procedure 1. Fill the reactor with purified deuterated acetylene (approximately 0.09 mol of gas) and urea.
2. Establish freeze-thaw cycles by varying the temperature between -21 and 5°C (2 hours at -21°C,
ramping to 5°C at 0.1°Cmin-1 and 2 hours at 5°C) by using a Haake Phoenix II programmable cryostat
(Thermo Electron Corporation).
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[Reactant]
SciFinder® Page 9

3 3.1 S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, 5°C photochemical, mercury vapor
discharge lamp used, global time of 3
weeks with initial 72h UV irradiation,
Reactants: 2, Solvents: 1, Steps: 1,
Stages: 1
Reaction Protocol
Step 3
Procedure 1. Fill the reactor with purified hydantoin and urea.
ramping to 5°C at 0.1°Cmin-1 and 2 hours at 5°C) using a Haake Phoenix II programmable cryostat
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Source
A New Route for the Prebiotic
Synthesis of Nucleobases and
Hydantoins in Water/Ice Solutions
Involving the Photochemistry of
Acetylene
Menor-Salvan, Cesar; Marin-Yaseli,
Margarita R.
Chemistry - A European Journal
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Centro de Astrobiologia (CSIC-INTA)
Torrejon de Ardoz, Spain 28850
Number of Steps
3
17. 3 Steps
SciFinder® Page 10

1.1 R:H2O Stages: 1

SciFinder® Page 11
2 photochemical, mercury vapor
2.1 R:NH3, S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, discharge lamp used, global time of 3
5°C weeks with initial 72h UV irradiation,
Reactants: 1, Reagents: 1, Solvents: 1,
Additional Product(s): Steps: 1, Stages: 1
Reaction Protocol
SciFinder® Page 12
Step 2
Procedure 1. Fill the reactor with purified acetylene (approximately 0.09 mol of gas) and ammonia.
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[Reactant]

Stages: 1
Reaction Protocol
SciFinder® Page 13
Step 3
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
3
18. 3 Steps

1.1 R:H2O Stages: 1
SciFinder® Page 14
[Reactant] [Reactant]
2 2.1 S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, 5°C global time of 3 weeks, Reactants: 3,
Additional Product(s): Solvents: 1, Steps: 1, Stages: 1
Reaction Protocol
SciFinder® Page 15
Step 2
Procedure 1. Fill the reactor with purified acetylene (approximately 0.09 mol of gas), urea and glyoxal.
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Experimental
Data
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[Reactant]

Stages: 1
Reaction Protocol
SciFinder® Page 16
Step 3
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
3
19. 3 Steps

1.1 R:H2O Stages: 1
SciFinder® Page 17
[Reactant]

SciFinder® Page 18
2 2.1 S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, 5°C photochemical, other products also
detected, mercury vapor discharge lamp
used, sealed and thermostated glass
reactor used, global time of 3 weeks
with initial 72h UV irradiation, Reactants:
2, Solvents: 1, Steps: 1, Stages: 1
SciFinder® Page 19
SciFinder® Page 20
SciFinder® Page 21
SciFinder® Page 22
Reaction Protocol
Step 2
Procedure 1. Fill the reactor with purified acetylene (approximately 0.09 mol of gas) and urea.
2. Establish the freeze-thaw cycles by varying temperature between -21 and 5°C (2 hours at -21°C,
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Experimental
Data
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[Reactant]
SciFinder® Page 23

Stages: 1
Reaction Protocol
Step 3
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
3
20. 2 Steps
SciFinder® Page 24

1.1 R:H2O Stages: 1
[Reactant]
SciFinder® Page 25

Reaction Protocol
SciFinder® Page 26
Step 2
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Experimental
Data
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
2
21. 2 Steps

SciFinder® Page 27
1 photochemical, mercury vapor
1.1 R:NH3, S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, discharge lamp used, global time of 3
5°C weeks with initial 72h UV irradiation,
Additional Product(s): Steps: 1, Stages: 1
Reaction Protocol
SciFinder® Page 28
Step 1
Procedure 1. Fill the reactor with purified acetylene (approximately 0.09 mol of gas) and ammonia.
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[Reactant]

Stages: 1
Reaction Protocol
SciFinder® Page 29
Step 2
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
2
22. 2 Steps

SciFinder® Page 30
1 1.1 S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, 5°C photochemical, sealed and
thermostated glass reactor used,
mercury vapor discharge lamp used,
global time of 3 weeks with initial 72h
UV irradiation, Reactants: 2, Solvents:
SciFinder® Page 31
SciFinder® Page 32
SciFinder® Page 33
Reaction Protocol
Step 1
Procedure 1. Fill the reactor with purified deuterated acetylene (approximately 0.09 mol of gas) and urea.
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Experimental
Data
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[Reactant]
SciFinder® Page 34

Stages: 1
Reaction Protocol
Step 2
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
2
23. 2 Steps
SciFinder® Page 35

SciFinder® Page 36
1 1.1 S:H2O, 2 h, -21°C; -21°C → 5°C; 2 h, 5°C global time of 3 weeks, Reactants: 3,
Additional Product(s): Solvents: 1, Steps: 1, Stages: 1
Reaction Protocol
SciFinder® Page 37
Step 1
Procedure 1. Fill the reactor with purified acetylene (approximately 0.09 mol of gas), urea and glyoxal.
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Experimental
Data
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[Reactant]

Stages: 1
Reaction Protocol
SciFinder® Page 38
Step 2
View more...
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
2
24. 2 Steps

SciFinder® Page 39
SciFinder® Page 40
SciFinder® Page 41
SciFinder® Page 42
SciFinder® Page 43
Reaction Protocol
Step 1
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Experimental
Data
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[Reactant]
SciFinder® Page 44

Stages: 1
Reaction Protocol
Step 2
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
2
25. Single Step
SciFinder® Page 45

Stages: 1
Transformation:
1. Oxidation of Methyl/Methylene to
Carbonyl
Reaction Protocol
Step 1
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SciFinder® Page 46
Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
1
26. Single Step
SciFinder® Page 47

SciFinder® Page 48
Transformation:
Uncategorized
Reaction Protocol
Step 1
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Experimental
Data
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Source
Acetylene
Margarita R.
Volume 19
Issue 20
Pages 6488-6497
Journal
2013
Number of Steps
1
27. 2 Steps
SciFinder® Page 49

1 Reactants: 1, Reagents: 3, Catalysts: 1,
1.1 R:HCl, R:O2, C:11104-93-1, S:H2O, rt → 45°C Solvents: 1, Steps: 1, Stages: 2
1.2 R:NaNO2, S:H2O, 45°C; 2 h, 45°C
[Reactant]

2 2.1 45°C → 75°C; 3 h, 75°C Reactants: 2, Steps: 1, Stages: 1
Source
New process for allantoin synthesis
Li, Ping; Guo, Wali; Wang, Xiaobing
Xiandai Huagong
Volume 31
Issue 12
Pages 53-55, 57
Journal
2011
School of Chemical Engineering
Technology
Shenyang, Peop. Rep. China 110142
Number of Steps
2
28. Single Step
SciFinder® Page 50

1.1 R:HCl, R:O2, C:11104-93-1, S:H2O, rt → 45°C 62%
stoichiometry, temperature and time,
Reactants: 2, Reagents: 3, Catalysts: 1,
1.2 R:NaNO2, S:H2O, 45°C; 2 h, 45°C Solvents: 1, Steps: 1, Stages: 3
1.3 45°C → 75°C; 3 h, 75°C
Transformation:
Uncategorized
Source
Xiandai Huagong
Volume 31
Issue 12
Pages 53-55, 57
Journal
2011
Technology
Number of Steps
1
29. Single Step

SciFinder® Page 51
1 1.1 45°C → 75°C; 3 h, 75°C Reactants: 2, Steps: 1, Stages: 1
Transformation:
Source
Xiandai Huagong
Volume 31
Issue 12
Pages 53-55, 57
Journal
2011
Technology
Number of Steps
1
30. Single Step

1 1.1 C:H3PO4, S:H2O, 4 h, 80°C optimization study, optimized on 62%
stoichiometry, temperature, time and
catalyst, Reactants: 2, Catalysts: 1,
Solvents: 1, Steps: 1, Stages: 1
Transformation:
SciFinder® Page 52
Source
Synthesis process optimization of
allantoin by orthogonal experiment
Liu, Li-xiu; He, Ai-jiang; Li, Xiang-biao
Guangzhou Huagong
Volume 39
Issue 9
Pages 116-118, 122
Journal
2011
Yibin Vocational & Technical College
Sichuan Yibin, Peop. Rep. China
644003
Number of Steps
1
31. Single Step

1 1.1 C:1112933-78-4, S:H2O, rt → 50°C; 6.5 h, ionic liquid used (catalyst), catalyst
50°C → 68°C 70%
prepared and used, Reactants: 2,
Stages: 1
Transformation:
Source
Process for synthesis of allantoin
Hu, Wenjing; Pan, Yongmei
China
2012
Patent Information
Aug 01, 2012
CN 102617476
A
SciFinder® Page 53
Number of Steps
1
32. Single Step

1 1.1 C:1041196-76-2, S:H2O, rt → 50°C; 6.5 h, ionic liquid used (catalyst), catalyst
50°C → 68°C 71%
Stages: 1
Transformation:
Source
China
2012
Patent Information
Aug 01, 2012
CN 102617476
A
Number of Steps
1
33. Single Step
SciFinder® Page 54

1 1.1 C:920537-20-8, S:H2O, rt → 50°C; 6.5 h, 50°C ionic liquid used (catalyst), catalyst
→ 68°C 43%
prepared and used, alternative reaction
conditions gave lower yield, Reactants:
2, Catalysts: 1, Solvents: 1, Steps: 1,
Stages: 1
Transformation:
Source
China
2012
Patent Information
Aug 01, 2012
CN 102617476
A
Number of Steps
1
34. Single Step

SciFinder® Page 55
→ 68°C 72%
Stages: 1
Transformation:
Source
China
2012
Patent Information
Aug 01, 2012
CN 102617476
A
Number of Steps
1
35. Single Step

→ 68°C 73%
Stages: 1
Transformation:
Source
China
2012
SciFinder® Page 56
Patent Information
Aug 01, 2012
CN 102617476
A
Number of Steps
1
36. Single Step

1 1.1 C:827320-59-2, S:H2O, rt → 50°C; 6.5 h, 50°C alternative reaction conditions gave
→ 68°C 76%
lower yield, ionic liquid used (catalyst),
catalyst prepared and used, Reactants:
2, Catalysts: 1, Solvents: 1, Steps: 1,
Stages: 1
Transformation:
Source
China
2012
Patent Information
Aug 01, 2012
CN 102617476
A
Number of Steps
1
37. Single Step
SciFinder® Page 57

1 1.1 C:La2O3, C:SiO2, C:ZrO2, C:H2SO4, S:H2O, 5 solid-supported catalyst, lanthanum
h, 75°C 46%
oxide doped sulfated silica-zirconium
prepared and used as solid acid
catalyst, optimization study, optimized
on stoichiometry of lanthanum oxide,
molar ratio of urea and glyoxalic acid,
reaction time and temperature and
amount of catalyst, Reactants: 2,
Stages: 1
Transformation:
Source
SO42-/La2O3-SiO2-ZrO2
Liu, Lixiu; He, Aijiang; Li, Xiangbiao
Asian Journal of Chemistry
Volume 24
Issue 5
Pages 2298-2300
Journal
2012
Department of Biological and
Chemical Engineering
Yibin Vocational and Technical
College
Yibin, Sichuan, Peop. Rep. China
644003
Number of Steps
1
38. Single Step
SciFinder® Page 58

1 1.1 C:H3PO3, C:H2NSO3H, S:H2O, rt green chemistry, other reaction
1.2 S:(CO2H)2, 2 h, 15°C; 1 h, 15°C; 1 h, 15°C → 64%
conditions gave lower yield, Reactants:
95°C; 2 h, 96-100°C; 100°C → 15°C 2, Catalysts: 2, Solvents: 2, Steps: 1,
Stages: 2
Transformation:
Source
Process for preparation of allantoin
from glyoxylic acid and urea with
phosphonic acid and sulfamic acid as
catalysts
Li, Jiansheng; Wu, Jing; Wen,
Hongjie; Zhang, Min
Assignee Tianjin Vocational Institute,
Peop. Rep. China
2011
Patent Information
Apr 13, 2011
CN 102010372
A
Number of Steps
1
39. Single Step

SciFinder® Page 59
1 1.1 C:TiO2, C:14808-79-8, rt → 75°C; 4 h, 75°C optimization study, optimized on 56%
catalyst, stoichiometry, SO4(2-)/TiO2-
HZSM-5 catalyst prepared and used,
Reactants: 2, Catalysts: 2, Steps: 1,
Stages: 1
Transformation:
Source
Preparation of solid acid SO42-/TiO2-
HZSM-5 and its application in the
synthesis of allantoin
Fu, Xinling; Xu, Haifeng; Zeng, Ming
Jingxi Huagong Zhongjianti
Volume 40
Issue 4
Pages 46-50
Journal
2010
Changsha Medical University
Changsha, Hunan Province, Peop.
Rep. China 410219
Number of Steps
1
40. 3 Steps

1 regioselective, Reactants: 2, Reagents:
1.1 R:KBH4, 30 min, rt; 1 h, rt 77% / 8%
8%
SciFinder® Page 60

2.1 R:SOCl2, 2 h, reflux; cooled 69%
Stages: 1
[Reactant]

3 3.1 S:MeNO2, reflux; 1 h, reflux; cooled Reactants: 2, Solvents: 1, Steps: 1, 15%
Stages: 1
Source
Synthesis of highly pure 14C-labeled
DL-allantoin and 13C NMR analysis
of labeling integrity
Patching, Simon G.
Journal of Labelled Compounds and
Radiopharmaceuticals
Volume 52
Issue 9
Pages 401-404
Journal
2009
Astbury Centre for Structural
Molecular Biology and Institute of
Membrane and Systems Biology
University of Leeds
Leeds, UK LS2 9JT
Number of Steps
3
41. 2 Steps
SciFinder® Page 61

1.1 R:SOCl2, 2 h, reflux; cooled 69%
Stages: 1
[Reactant]

Stages: 1
Source
Patching, Simon G.
Volume 52
Issue 9
Pages 401-404
Journal
2009
University of Leeds
Leeds, UK LS2 9JT
Number of Steps
2
42. Single Step
SciFinder® Page 62

Stages: 1
Transformation:
1. N-Alkylation of Amides/ Imides or
Mitsunobu Reaction
Source
Patching, Simon G.
Volume 52
Issue 9
Pages 401-404
Journal
2009
University of Leeds
Leeds, UK LS2 9JT
Number of Steps
1
43. Single Step
SciFinder® Page 63
1 green chemistry, optimization study,
1.1 R:NaOH, S:H2O, pH 8 42%
optimized on stoichiometry, time and
temperature, Reactants: 2, Reagents: 2,
1.2 R:H2O2, S:H2O, 1.0 h, 44°C; 2.0 h, 44°C Solvents: 1, Steps: 1, Stages: 3
1.3 S:H2O, 3 h, 70°C
Transformation:
Uncategorized
Source
Synthesis of allantoin by glyoxal
oxidation and condensation method
Hu, Zhen; Yu, Hailian
Sichuan Huagong
Volume 11
Issue 4
Pages 1-4, 27
Journal
2008
Department of Material and Chemical
Engineering
Sichuan University of Science and
Engineering
Zigong, Peop. Rep. China 643000
Number of Steps
1
44. 3 Steps

1 Reactants: 2, Reagents: 2, Solvents: 1,
1.1 R:NaHCO3, S:H2O, rt; 30 min, cooled; 30 min, Steps: 1, Stages: 2
80°C; 80°C → rt
1.2 R:HCl, S:H2O, pH 4
Experimental Procedure
SciFinder® Page 64
Synthesis of Dansyl Chloride-13C2. The synthesis of 13C-dansyl chloride as a derivatizing reagent was
based on a two-step procedure described by Horner and Bergmann.58,59 Figure 1A shows the
synthesis scheme. In a 25 mL round-bottom flask, 0.78 g of 5-aminonaphthalene-1-sulfonic acid was
added slowly in portions to 1.09 g of sodium bicarbonate in 3.5 mL of water. Then 0.77 mL of 13C2-
dimethyl sulfate was added dropwise over 30 min to the stirred ice-cooled solution. The solution was
warmed to 80 °C in a hot water-bath for 30 min. After cooling to room temperature, 0.46 mL of
concentrated hydrochloric acid was added to the solution, and the pH was adjusted to 4. The
precipitated product, 5-dimethylamino-naphthalene-1-sulfonic acid was filtered, washed with a small
quantity of water, dried in the air to a constant weight, and then further dried at 120 °C in an oven. 5-
dimethylamino-naphthalene-1-sulfonic acid
Reaction Protocol
Step 1
Procedure 1. Add 0.78 g of 5-aminonaphthalene-1-sulfonic acid in portions to 1.09 g of sodium bicarbonate in 3.5
mL of water into a 25 mL round-bottom flask.
2. Add 0.77 mL of 13C2-dimethyl sulfate dropwise to the stirred ice-cooled solution over 30 minutes.
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2.1 R:PCl5, 2 h, 60°C Steps: 1, Stages: 2
2.2 R:NaHCO3, S:H2O, neutralized
Under ice-cooling, 5-dimethylamino-naphthalene-1-sulfonic acid was ground into a powder and then
mixed with 0.88 g of phosphorus pentachloride. To complete the reaction, the mixture was warmed to
60 °C for 2 h under the exclusion of moisture. About 12.5 mL of ice water was then poured in. After
careful neutralization with 1.75 g of sodium bicarbonate, the product was extracted with Et2O (4 × 6
mL). The organic layer was dried using sodium sulfate. The residue was purified by flush
chromatography (silica gel, 20 cm × 3 cm, 60 mL of AcOEt) and further purified by a semipreparative
Grace Apollo silica normal-phase HPLC column (10 mm × 150 mm, 5 µm particles). The resulting
product of 13C-dansyl chloride was then dried in a SpeedVac and stored in a -80 °C freezer. The
purity and confirmation of 13C-dansyl chloride was tested against the commercial 12C-dansyl chloride
using LC/FTICR MS. NMR was also used to characterize the reaction products and confirm the
identity and purity of the final product. 13C-dansyl chloride
Reaction Protocol
SciFinder® Page 65
Step 2
Procedure 1. Grind 5-dimethylamino-naphthalene-1-sulfonic acid into a powder under ice-cooling.
2. Mix the mixture with 0.88 g of phosphorus pentachloride.
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[Reactant]
13C
2-dansyl derivs.

3 3.1 S:H2O, 60 min, 60°C, pH 9.4 combinatorial, alternate unlabeled
preparation also shown, sodium
3.2 R:MeNH2, 30 min, 60°C carbonate buffered solution used,
Steps: 1, Stages: 2
General/Typical Procedure: Dansylation Labeling Reaction. Figure 1B shows the reaction scheme for
dansylation of amine- and phenol-containing compounds. The frozen urine was thawed in an ice-bath
and then centrifuged for 10 min at 12 000 rpm. About 100 µL of urine supernatant or amino acids,
amine, and phenolic hydroxyl standard solutions were mixed with an equal volume of sodium
carbonate/sodium bicarbonate buffer (0.5 mol/L, pH 9.4) in a reaction vial. The solutions were
vortexed, spun down, and mixed with 100 µL of freshly prepared 12C-dansyl chloride solution (20
mg/mL) (for light labeling) or 13C-dansyl chloride (20 mg/mL) (for heavy labeling). The dansylation
reaction was allowed to proceed for 60 min at 60 °C with shaking at 150 rpm in an Innova-4000
benchtop incubator shaker. After 60 min, mixtures were vortexed, spun down and 30 µL of
methylamine (0.5 mol/L) was added to the reaction mixture to consume the excess dansyl chloride.
The solutions were again vortexed and spun down. After an additional 30 min of 60 °C incubation,
samples were then centrifuged. The 13C-labeled mixtures were combined with their 12C-labeled
counterparts for MS analysis. The reaction vials were carefully washed twice using 50 µL of LC/MS
grade MeOH, and the washing solution was added to the initial mixture to ensure dissolution and
transfer of all products for MS analysis. The combined mixtures were centrifuged for 10 min at 12 000
rpm and were ready to be injected onto a RPLC column. Dns-allantoin
Reaction Protocol
Step 3
Procedure 1. Thaw the frozen urine in an ice-bath.
2. Centrifuge the frozen urine for 10 minutes at 12 000 rpm.
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MethodsNow
SciFinder® Page 66
Source
Differential 12C-/13C-Isotope
Dansylation Labeling and Fast Liquid
Chromatography/Mass Spectrometry
for Absolute and Relative
Quantification of the Metabolome
Guo, Kevin; Li, Liang
Analytical Chemistry (Washington,
DC, United States)
Volume 81
Issue 10
Pages 3919-3932
Journal
2009
Department of Chemistry
University of Alberta
Edmonton, Can. T6G 2G2
Number of Steps
3
45. 2 Steps

1.1 R:PCl5, 2 h, 60°C Steps: 1, Stages: 2
1.2 R:NaHCO3, S:H2O, neutralized
Under ice-cooling, 5-dimethylamino-naphthalene-1-sulfonic acid was ground into a powder and then
mixed with 0.88 g of phosphorus pentachloride. To complete the reaction, the mixture was warmed to
60 °C for 2 h under the exclusion of moisture. About 12.5 mL of ice water was then poured in. After
careful neutralization with 1.75 g of sodium bicarbonate, the product was extracted with Et2O (4 × 6
mL). The organic layer was dried using sodium sulfate. The residue was purified by flush
chromatography (silica gel, 20 cm × 3 cm, 60 mL of AcOEt) and further purified by a semipreparative
Grace Apollo silica normal-phase HPLC column (10 mm × 150 mm, 5 µm particles). The resulting
product of 13C-dansyl chloride was then dried in a SpeedVac and stored in a -80 °C freezer. The
purity and confirmation of 13C-dansyl chloride was tested against the commercial 12C-dansyl chloride
using LC/FTICR MS. NMR was also used to characterize the reaction products and confirm the
identity and purity of the final product. 13C-dansyl chloride
SciFinder® Page 67
Reaction Protocol
Step 1
Procedure 1. Grind 5-dimethylamino-naphthalene-1-sulfonic acid into a powder under ice-cooling.
2. Mix the mixture with 0.88 g of phosphorus pentachloride.
View more...
View with
MethodsNow
[Reactant]
13C
2-dansyl derivs.

Steps: 1, Stages: 2
Reaction Protocol
Step 2
View more...
View with
MethodsNow
SciFinder® Page 68
Source
DC, United States)
Volume 81
Issue 10
Pages 3919-3932
Journal
2009
Number of Steps
2
46. Single Step
13C
2-dansyl derivs.

Steps: 1, Stages: 2
Transformation:
Uncategorized
SciFinder® Page 69
Reaction Protocol
Step 1
View more...
View with
MethodsNow
Source
DC, United States)
Volume 81
Issue 10
Pages 3919-3932
Journal
2009
Number of Steps
1
47. Single Step
SciFinder® Page 70

1.1 R:HNO3, S:H2O, rt → 55°C; 55°C; 6 h, 55°C 68%
stoichiometry, temperature and reaction
1.2 4.5 h, 75°C time, Reactants: 2, Reagents: 1,
Transformation:
Uncategorized
Source
Preparation of allantoin by oxidation
of glyoxal with nitric acid
Lei, Yanbin; Jia, Ying
Huagong Shikan
Volume 21
Issue 7
Pages 19-21
Journal
2007
503 Section
Second Artillery Engineering Institute
Xi'an, Peop. Rep. China 710025
Number of Steps
1
48. Single Step

SciFinder® Page 71
1 1.1 C:H2SO4, C:H3PO4, S:H2O, S:EtOH, S:THF, rt optimization study, optimized on solvent, 89%
→ 75°C; 4 h, 75°C catalyst, ratio of reactants and time,
Reactants: 2, Catalysts: 2, Solvents: 3,
Steps: 1, Stages: 1
Transformation:
Source
Study on synthesis of N-(2,5-dioxo-4-
imidazolidinyl)urea (allantoin)
Pei, Lei; Liu, Fusheng; Yu, Shitao
Qingdao Keji Daxue Xuebao, Ziran
Kexueban
Volume 29
Issue 2
Pages 106-109
Journal
2008
Qingdao University of Science and
Technology
Qingdao, Peop. Rep. China 266042
Number of Steps
1
49. 2 Steps

1 alternative reaction conditions shown,
1.1 R:KOH, S:MeOH, 75°C; 6 h, 75°C Reactants: 1, Reagents: 2, Solvents: 2,
Steps: 1, Stages: 2
1.2 R:HCl, S:H2O, neutralized
SciFinder® Page 72
[Reactant]

2 other reaction condition gave lower
2.1 R:HCl, S:H2O, 4 h, 75°C; 75°C → rt 62%
yield, Reactants: 2, Reagents: 1,
Source
New process for synthesizing
allantoin
Sang, Wenqiang
Assignee Qingzhou Ailitong
Chemicals Technical Co., Ltd., Peop.
Rep. China
2008
Patent Information
Dec 24, 2008
CN 101328149
A
Number of Steps
2
50. 2 Steps

1 alternative reaction conditions shown,
1.1 R:NaOH, S:MeOH, 1 h, rt; 70°C; 6 h, 70°C Reactants: 1, Reagents: 2, Solvents: 2,
Steps: 1, Stages: 2
1.2 R:HCl, S:H2O
SciFinder® Page 73
[Reactant]

2.1 R:HCl, S:H2O, 6 h, 90°C temperature, reaction time and reagent,
Steps: 1, Stages: 1
Source
allantoin
Sang, Wenqiang
Rep. China
2008
Patent Information
Dec 24, 2008
CN 101328149
A
Number of Steps
2
51. Single Step

SciFinder® Page 74
1 1.1 C:Ca(OH)2, S:H2O, 40°C; 12 h, 40°C Reactants: 2, Reagents: 1, Catalysts: 1, 62%
1.2 R:HNO3, S:H2O
Transformations:
1.3 R:HNO3, S:H2O, 6 h, 70°C
Mitsunobu Reaction
Source
allantoin
Sang, Wenqiang
Rep. China
2008
Patent Information
Dec 24, 2008
CN 101328149
A
Number of Steps
1
52. Single Step

1 other reaction condition gave lower
1.1 R:HCl, S:H2O, 4 h, 75°C; 75°C → rt 62%
yield, Reactants: 2, Reagents: 1,
Transformations:
Mitsunobu Reaction
SciFinder® Page 75
Source
allantoin
Sang, Wenqiang
Rep. China
2008
Patent Information
Dec 24, 2008
CN 101328149
A
Number of Steps
1
53. Single Step

1.1 R:HCl, S:H2O, 6 h, 90°C temperature, reaction time and reagent,
Steps: 1, Stages: 1
Transformations:
Mitsunobu Reaction
Source
allantoin
Sang, Wenqiang
Rep. China
2008
SciFinder® Page 76
Patent Information
Dec 24, 2008
CN 101328149
A
Number of Steps
1
54. Single Step

1 1.1 C:1343-93-7, rt → 75°C; 20 min, 75-80°C; 3 h, Reactants: 2, Reagents: 1, Catalysts: 1, 50%
75-80°C Steps: 1, Stages: 2
1.2 R:H2O, cooled Transformation:
Source
Synthesis of allantoin without catalyst
Gong, Hong; Wang, Min; Jiang, Heng;
Wang, Zhi-chang
Hecheng Huaxue
Volume 14
Issue 4
Pages 395-397
Journal
2006
School of Petroleum and Chemical
Technology
Liaoning University of Petroleum and
Chemical Technology
Fushun, Peop. Rep. China 113001
Number of Steps
1
55. Single Step
SciFinder® Page 77

1 1.1 C:73640-08-1, rt → 75°C; 20 min, 75-80°C; 3 h, Reactants: 2, Reagents: 1, Catalysts: 1,
75-80°C 62%
Steps: 1, Stages: 2
Source
Wang, Zhi-chang
Hecheng Huaxue
Volume 14
Issue 4
Pages 395-397
Journal
2006
Technology
Chemical Technology
Number of Steps
1
56. Single Step

SciFinder® Page 78
1 1.1 C:MeSO3H, rt → 75°C; 20 min, 75-80°C; 3 h, Reactants: 2, Reagents: 1, Catalysts: 1, 65%
75-80°C Steps: 1, Stages: 2
Source
Wang, Zhi-chang
Hecheng Huaxue
Volume 14
Issue 4
Pages 395-397
Journal
2006
Technology
Chemical Technology
Number of Steps
1
57. Single Step

1 1.1 rt → 60°C; 20 min, 60°C; 3 h, 60°C optimization study, optimized on ratio of 60%
materials, reaction temperature, raction
1.2 R:H2O, cooled time, green chemistry-waste reduction,
Reactants: 2, Reagents: 1, Steps: 1,
Stages: 2
Transformation:
SciFinder® Page 79
Source
Wang, Zhi-chang
Hecheng Huaxue
Volume 14
Issue 4
Pages 395-397
Journal
2006
Technology
Chemical Technology
Number of Steps
1
58. 2 Steps

1.1 R:NaOH, S:H2O, pH 7.5-8 Steps: 1, Stages: 2
1.2 R:H2O2, S:H2O
[Reactant]

SciFinder® Page 80
2 2.1 C:TiO2 sulfated, C:SiO2, rt → 75°C; 3 h, 75°C solid-supported catalyst, silica gel used, 65%
optimization study, optimized on amount
of catalyst and time, superacidic,
Stages: 1
Source
Catalytic synthesis of allantoin by
solid super acid SO42-/TiO2-SiO2
Yan, Dongying; Wang, Jikui
Jingxi Shiyou Huagong Jinzhan
Volume 7
Issue 7
Pages 17-18, 26
Journal
2006
Department of Applied Chemistry
Nanjing University of Technology
Nanjing, Peop. Rep. China 210009
Number of Steps
2
59. Single Step

1 1.1 C:TiO2 sulfated, C:SiO2, rt → 75°C; 3 h, 75°C solid-supported catalyst, silica gel used, 65%
optimization study, optimized on amount
of catalyst and time, superacidic,
Stages: 1
Transformation:
SciFinder® Page 81
Source
Catalytic synthesis of allantoin by
solid super acid SO42-/TiO2-SiO2
Yan, Dongying; Wang, Jikui
Volume 7
Issue 7
Pages 17-18, 26
Journal
2006
Department of Applied Chemistry
Number of Steps
1
60. Single Step

1 1.1 C:HCl, C:HCO2H, S:H2O, rt → 75°C; 3 h, 75°C optimization study, optimized on 68%
reaction time, temperature, catalyst,
stoichiometry, alternate acid described
as catalyst, Reactants: 2, Catalysts: 2,
Transformation:
Source
Synthesis and characterization of
allantoin
Cheng, Qin; Cui, Huhui; Zhang, Lei;
Sun, Yanxia; Yin, Haibin; Che, Jitai
Volume 6
Issue 9
Pages 17-19
Journal
2005
SciFinder® Page 82
Dalian Guanghui Chem. Co., Ltd.
Dalian, Peop. Rep. China 116113
Number of Steps
1
61. Single Step

1 1.1 8 h, 70°C ion-exchange resin used as catalyst, 70%
optimization study, optimized on
catalyst, catalyst amount, the ratio of
stoichiometry and temperature,
Transformation:
Source
Synthesis of allantoin using ion
exchange resin as catalyst
Jin, Limin; Wu, Sufang
Huaxue Fanying Gongcheng Yu
Gongyi
Volume 21
Issue 5
Pages 427-431
Journal
2005
Department of Chemical and
Biological Engineering
Zhejiang University
Hangzhou, Peop. Rep. China 310027
Number of Steps
1
SciFinder® Page 83
62. Single Step

1 1.1 C:HCl, C:H2SO4, C:81319-51-9, C:H3PO4, optimization study, optimized on
S:H2O, rt → 75°C; 3.5 h, 75°C; 12 h, rt 69%
catalyst, ratio of reactants, time and
temperature, Reactants: 2, Catalysts: 4,
Transformation:
Source
Synthesis of allantoin
Cheng, Qin; Zhang, Lei; Sun, Yan-xia;
Cui, Hu-hui; Yin, Hai-bin; Che, Ji-tai
Jiangsu Huagong
Volume 33
Issue Suppl.
Pages 116-118
Journal
2005
Dalian Guanghui Chemical Co., Ltd.
Dalian, Peop. Rep. China 116113
Number of Steps
1
63. Single Step

SciFinder® Page 84
1 1.1 rt → 70°C; 9 h, 70°C strong acidic cation exchange resin 69%
CT275 used as catalyst, optimization
study, optimized on catalyst, Reactants:
Transformation:
Source
Environment friendly process for
preparation of allantoin
Wu, Sufang; Jin, Limin
Assignee Zhejiang University, Peop.
Rep. China
2006
Patent Information
May 03, 2006
CN 1765888
A
Number of Steps
1
64. Single Step

1 1.1 C:HCl, S:H2O, 4 h, 75-80°C Reactants: 2, Catalysts: 1, Solvents: 1, 33%
Steps: 1, Stages: 1
Transformation:
SciFinder® Page 85
Source
Study on the synthesis of allantoin
with a composite acid of PTSA/H3P04
as catalyst
Cai, Zhaosheng; Wang, Jintang; Qiu,
Ligan; Wang, Maoyuan
Huaxue Shijie
Volume 45
Issue 1
Pages 42-44, 38
Journal
2004
School of Science
Number of Steps
1
65. Single Step

1 1.1 C:H3PO4, S:H2O, 4 h, 75-80°C Reactants: 2, Catalysts: 1, Solvents: 1, 43%
Steps: 1, Stages: 1
Transformation:
Source
as catalyst
Huaxue Shijie
Volume 45
Issue 1
Pages 42-44, 38
Journal
2004
SciFinder® Page 86
School of Science
Number of Steps
1
66. Single Step

1 1.1 C:p-MeC6H4SO3H, S:H2O, 4 h, 75-80°C Reactants: 2, Catalysts: 1, Solvents: 1, 46%
Steps: 1, Stages: 1
Transformation:
Source
as catalyst
Huaxue Shijie
Volume 45
Issue 1
Pages 42-44, 38
Journal
2004
School of Science
Number of Steps
1
67. Single Step
SciFinder® Page 87

1 1.1 C:p-MeC6H4SO3H, C:H3PO4, S:H2O, 7 h, Reactants: 2, Catalysts: 2, Solvents: 1,
75-80°C 61%
Steps: 1, Stages: 1
Transformation:
Source
as catalyst
Huaxue Shijie
Volume 45
Issue 1
Pages 42-44, 38
Journal
2004
School of Science
Number of Steps
1
68. Single Step

SciFinder® Page 88
1 1.1 C:p-MeC6H4SO3H, C:H3PO4, S:H2O, 3.5 h, optimization study, Reactants: 2,
85°C 59%
Stages: 1
Transformation:
Source
Optimization of synthetic condition of
allantoin with complex acid consisted
of o-toluenesulfonic acid and
phosphoric acid as catalyst
Yang, Wei; Cai, Zhaosheng
Guangzhou Huagong
Volume 32
Issue 2
Pages 18-24
Journal
2004
Department of Police Science and
Technology
Jiangsu Officer College
Number of Steps
1
69. 2 Steps

1 Go to Science of Synthesis, a critically
1.1
reviewed reference work of synthetic
methodology, for more information.,

SciFinder® Page 89
2.1
Source
Product class 17: purines
Seela, F.; Ramzaeva, N.; Rosemeyer,
H.
Science of Synthesis
Volume 16
Pages 945-1108
Journal; General Review
2004
Number of Steps
2
70. Single Step

1.1
Transformation:
Uncategorized
Source
Product class 17: purines
Seela, F.; Ramzaeva, N.; Rosemeyer,
H.
Science of Synthesis
Volume 16
Pages 945-1108
Journal; General Review
2004
Number of Steps
1
SciFinder® Page 90
71. Single Step

1 regioselective, green chemistry,
1.1 R:H2O2, C:12067-99-1, S:H2O, 5°C; 5 h, 5°C; 59%
optimization study, optimized on
1 h, 5°C temperature and stoichiometry,
industrial, Reactants: 2, Reagents: 1,
1.2 5°C → 70°C; 20 min, 70°C; 20 min, 70°C; 2 h, Catalysts: 1, Solvents: 1, Steps: 1,
75-80°C Stages: 2
Transformation:
Uncategorized
Source
Research on the synthesis of allantoin
Li, Hai-jing; Xue, Zheng-ran
Shandong Huagong
Volume 33
Issue 3
Pages 10-11
Journal
2004
Shandong Chemical Industry
Research Institute
Jinan, Peop. Rep. China 250014
Number of Steps
1
72. 3 Steps

SciFinder® Page 91
1 optimization study, optimized on molar
1.1 R:HNO3, R:NaNO2, S:H2O, rt → 40°C 46%
ratio of reactants,reaction temperature
and time, Reactants: 1, Reagents: 2,
1.2 R:HNO3, S:H2O, 38-40°C; 40°C → 55°C; 6 h, Solvents: 1, Steps: 1, Stages: 2
55°C

2.1 R:CaCl2, R:NaOH, S:H2O, pH 0.6; pH 1.0 95%
Steps: 1, Stages: 2
2.2 R:NaOH, S:H2O, pH 1.9; pH 3.5
[Reactant]

3 28% overall yield from Acetaldehyde,
3.1 R:HCl, S:H2O, rt → 70°C; 3 h, 70°C 65%
optimization study, optimized on molar
Source
Synthesis of allantoin using
acetaldehyde
He, Chuhua; Liu, Huijun; Li, Shan
Xiangliao Xiangjing Huazhuangpin
Issue 3
Pages 17-19
Journal
2003
SciFinder® Page 92
College of Chemistry and Chemical
Engineering
Nanhua University
Hengyang, Peop. Rep. China 421001
Number of Steps
3
73. 2 Steps

1.1 R:CaCl2, R:NaOH, S:H2O, pH 0.6; pH 1.0 95%
Steps: 1, Stages: 2
1.2 R:NaOH, S:H2O, pH 1.9; pH 3.5
[Reactant]

2.1 R:HCl, S:H2O, rt → 70°C; 3 h, 70°C 65%
SciFinder® Page 93
Source
acetaldehyde
Issue 3
Pages 17-19
Journal
2003
Engineering
Nanhua University
Number of Steps
2
74. Single Step

1.1 R:HCl, S:H2O, rt → 70°C; 3 h, 70°C 65%
Transformation:
Source
acetaldehyde
Issue 3
Pages 17-19
Journal
2003
SciFinder® Page 94
Engineering
Nanhua University
Number of Steps
1
75. 3 Steps

1 optimization study, Reactants: 1,
1.1 R:AcONa, S:H2O, 48 h, reflux 69%
Reagents: 1, Solvents: 1, Steps: 1,
Stages: 1

2.1 R:CaCl2, R:NaOH, S:H2O, overnight, pH 6.0 Steps: 1, Stages: 1
3
SciFinder® Page 95
[Reactant]

3 30% overall yield from methyl
3.1 R:HCl, S:H2O, rt dichloroacetate, optimization study,
3.2 4 h, 75°C; 75°C → rt; overnight, rt Reactants: 2, Reagents: 1, Solvents: 1,
Steps: 1, Stages: 2
Source
Synthesis of allantoin from methyl
dichloroacetate
Liu, Ji-yan; Liu, Xue-qing
Huaxue Yu Shengwu Gongcheng
Volume 20
Issue 6
Pages 36-37
Journal
2003
College of Chemistry and Molecular
Sciences
Wuhan University
Wuhan, Peop. Rep. China 430072
Number of Steps
3
76. 2 Steps

1.1 R:CaCl2, R:NaOH, S:H2O, overnight, pH 6.0 Steps: 1, Stages: 1
SciFinder® Page 96
[Reactant]

Steps: 1, Stages: 2
Source
dichloroacetate
Volume 20
Issue 6
Pages 36-37
Journal
2003
Sciences
Wuhan University
Number of Steps
2
77. Single Step

SciFinder® Page 97
Steps: 1, Stages: 2
Transformation:
Source
dichloroacetate
Volume 20
Issue 6
Pages 36-37
Journal
2003
Sciences
Wuhan University
Number of Steps
1
78. Single Step

1 solid-supported catalyst, green chem.-
1.1 R:H2O2, C:FeSO4, S:H2O, 1 h, 15-20°C 54%
catalyst, optimization study, Reactants:
1.2 C:10294-54-9, C:9003-54-7, 4 h, 80°C 2, Reagents: 1, Catalysts: 3, Solvents:
Transformation:
Uncategorized
SciFinder® Page 98
Source
big-hole resin supported Ce(SO4)2
Chen, Xiaoyan; Ma, Lanying; Liu,
Wanyi; Tian, Danian
Ningxia Daxue Xuebao, Ziran
Kexueban
Volume 25
Issue 3
Pages 249-252
Journal
2004
School of Chemistry and Chemical
Engineering
Ningxia University
Yinchuan, Peop. Rep. China 750021
Number of Steps
1
79. Single Step

1 1.1 C:TiCl4, C:La2O3, 3 h, 73-75°C optimization study, solid-supported 75%
catalyst, Reactants: 2, Catalysts: 2,
Steps: 1, Stages: 1
Transformation:
Source
Synthesis of allantoin by
SO4+2%∓/TiO2-La+3++ rare-earth
solid superacid
Jin, Huafeng; Xiang, Jiming; Li,
Baozhang
Huaxue Yanjiu Yu Yingyong
Volume 15
Issue 3
Pages 381-382
Journal
2003
SciFinder® Page 99
Ankang Teacher's College
Ankang, Peop. Rep. China 725000
Number of Steps
1
80. Single Step

1 1.1 C:Ce sulfate reaction product with hydrogen optimization study, Reactants: 2,
peroxide, S:H2O, 25°C 54%
1.2 C:FeSO4 reaction product with hydrogen Stages: 2
peroxide, C:H2O2 reaction product with ferrous
sulfate, 80°C Transformation:
Uncategorized
Source
Allantoin synthesizing process
Liu, Wanyi; Chen, Xiaoyan; Tian,
Xiaoyan
Assignee Ningxia Univ., Peop. Rep.
China
2004
Patent Information
Sep 15, 2004
CN 1528749
A
Number of Steps
1
81. Single Step
SciFinder® Page 100

1 1.1 C:FeSO4 reaction product with hydrogen optimization study, Reactants: 2,
peroxide, C:H2O2 reaction product with ferrous 55%
sulfate, S:H2O, 20°C Stages: 4
1.2 4 h, 20°C
1.3 C:Ce sulfate reaction product with hydrogen Transformation:
peroxide, S:H2O, 22 h, rt; 5 h, 110°C
1.4 3-4 h, 70-85°C
Uncategorized
Source
Xiaoyan
China
2004
Patent Information
Sep 15, 2004
CN 1528749
A
Number of Steps
1
82. Single Step

1 1.1 C:H2O2 reaction product with ferrous sulfate, optimization study, Reactants: 2,
C:Ce sulfate reaction product with hydrogen 56%
peroxide, S:H2O, 20°C Stages: 4
1.2 4 h, 20°C
1.3 C:FeSO4 reaction product with hydrogen Transformation:
peroxide, S:H2O, 26 h, rt; 4 h, 100°C
1.4 3-4 h, 70-85°C
Uncategorized
Source
Xiaoyan
China
2004
Patent Information
Sep 15, 2004
CN 1528749
A
Number of Steps
1
83. Single Step

1 1.1 S:H2O, S:AcOH, 10 min, rt; 2-3 h, rt Reactants: 2, Solvents: 2, Steps: 1, 99%
Stages: 1
Transformation:
1. Addition of Amines to Isocyanates/
Isothiocyanates
Source
Synthesis of sulofenur analogs as
antitumour agents: Part II
Youssef, Khairia M.; Al-Abdullah,
Ebtihal; El-Khamees, Hamad
Medicinal Chemistry Research
Volume 11
Issue 9
Pages 481-503
Journal
2003
Department of Pharmaceutical
Chemistry, College of Pharmacy
King Saud University
Riyadh, Saudi Arabia 11451
Number of Steps
1
84. Single Step

1 optimization study, KPi buffered solution 94%/
1.1 R: used; optimized on type and amount of
oxidant, temperature, and pH; minor
product yield 0.09%; alternate reaction
conditions give increased yield of minor
product, Reactants: 1, Reagents: 1,
Steps: 1, Stages: 1
Transformation:
Uncategorized
30 min, rt, pH 6.7
General/Typical Procedure: Oxidation of Uric Acid by 2 equivalents of Na2 IrCl6 at Various
Temperatures. Uric acid (930 µM), labeled Spd (1.4 µM), and Na2IrCl6 (1.9 mM) were held in KPi
buffer (0.1 M, pH 7.4) at 0 °C, 24, 50, 62 and 84 °C for 30 min with stirring. Each oxidation was carried
out in duplicates with control experiments where no Na2IrCl6 was added. yield 94%
Source
Spirodihydantoin Is a Minor Product
of 5-Hydroxyisourate in Urate
Oxidation
Yu, Hongbin; Niles, Jacquin C.;
Wishnok, John S.; Tannenbaum,
Steven R.
Organic Letters
Volume 6
Issue 19
Pages 3417-3420
Journal
2004
Biological Engineering Division,
Massachusetts Institute of
Technology
Cambridge, USA 02139
Number of Steps
1
85. Single Step

1 optimization study, KPi buffered solution 40% / 1%
1.1 R: used; optimized on type and amount of
oxidant, temperature, and pH; alternate
reaction conditions give increased yield
of major product, Reactants: 1,
Reagents: 1, Steps: 1, Stages: 1
Transformation:
Uncategorized
30 min, 84°C, pH 8
Oxidation of Uric Acid by 2 equivalents of Na2 IrCl6 at Various Temperatures. Uric acid (930 µM),
labeled Spd (1.4 µM), and Na2IrCl6 (1.9 mM) were held in KPi buffer (0.1 M, pH 7.4) at 0 °C, 24, 50,
62 and 84 °C for 30 min with stirring. Each oxidation was carried out in duplicates with control
experiments where no Na2IrCl6 was added. yield 40%, 0.92%
Source
Spirodihydantoin Is a Minor Product
of 5-Hydroxyisourate in Urate
Oxidation
Yu, Hongbin; Niles, Jacquin C.;
Wishnok, John S.; Tannenbaum,
Steven R.
Organic Letters
Volume 6
Issue 19
Pages 3417-3420
Journal
2004
Biological Engineering Division,
Massachusetts Institute of
Technology
Cambridge, USA 02139
Number of Steps
1
86. Single Step

1 1.1 C:81319-51-9, C:H3PO4, S:H2O, 3 h, 75°C; 12 yield depends on reaction conditions,
h, rt 71%
Reactants: 2, Catalysts: 2, Solvents: 1,
Steps: 1, Stages: 1
Transformation:
Source
catalyzed by mixed acid
(H7PW12O42/H3PO4)
Cui, Zhimin; Chen, Xueheng; Ma,
Tongsen
Zhengzhou Gongcheng Xueyuan
Xuebao
Volume 23
Issue 2
Pages 35-36,48
Journal
2002
Department of Chemical Engineering
Wuyi University
Jiangmen, Guangdong Province,
Peop. Rep. China 529020
Number of Steps
1
87. Single Step

1 1.1 C:p-Tosyl chloride, 2 h, 80-85°C Reactants: 2, Catalysts: 1, Steps: 1, 70%
Stages: 1
Transformation:
Source
Synthesis of allantoin catalyzed by p-
toluenesulfochloride
Jin, Tong-shou; Wang, Zhen-hua;
Zhao, Yong-jie; Song, Xin-ru
Huaxue Shiji
Volume 25
Issue 5
Pages 303-304
Journal
2003
College of Chemistry and
Environmental Science
Hebei University
Baoding, Peop. Rep. China 071002
Number of Steps
1
88. Single Step

1 1.1 C:DOWEX 50W-X8, S:H2O, 17 h, 343K green chem.-catalyst, Reactants: 2, 92%
Stages: 1
Transformation:
Source
Heterogeneous catalysis in the
synthesis and reactivity of allantoin
Cativiela, Carlos; Fraile, Jose M.;
Garcia, Jose I.; Lazaro, Beatriz;
Mayoral, Jose A.; Pallares, Antonio
Green Chemistry
Volume 5
Issue 2
Pages 275-277
Journal
2003
Dept. de Quimica Organica, Inst. de
Ciencia de Materiales de Aragon
Universidad de Zaragoza
Zaragoza, Spain E-50009
Number of Steps
1
89. 2 Steps

1.1 R:FeSO4, R:H2O2, S:H2O, 2-3 h, 5-8°C; 0.5-10 Steps: 1, Stages: 1 86%
[Reactant]

2 2.1 C:1343-93-7, S:H2O, 2-3 h, 75-80°C Reactants: 2, Catalysts: 1, Solvents: 1, 69%
Steps: 1, Stages: 1
Source
Study of new technology of allantoin
synthesis
Shi, Gaofeng; He, Yanlin; Yang,
Yunshang; Lu, Runhua
Journal of Gansu University of
Technology (English Edition)
Volume E-6
Issue 1
Pages 163-166
Journal
2002
Lanzhou Institute of Chemical Physics
Chinese Academy of Sciences
Lanzhou, Peop. Rep. China 730000
Number of Steps
2
90. Single Step

1 1.1 C:1343-93-7, S:H2O, 2-3 h, 75-80°C Reactants: 2, Catalysts: 1, Solvents: 1, 69%
Steps: 1, Stages: 1
Transformation:
Source
Study of new technology of allantoin
synthesis
Shi, Gaofeng; He, Yanlin; Yang,
Yunshang; Lu, Runhua
Journal of Gansu University of
Technology (English Edition)
Volume E-6
Issue 1
Pages 163-166
Journal
2002
Lanzhou Institute of Chemical Physics
Chinese Academy of Sciences
Lanzhou, Peop. Rep. China 730000
Number of Steps
1
91. Single Step

1 Reactants: 2, Reagents: 1, Catalysts: 1, 30%
1.1 R:H2O2, S:H2O, 2 h, 40-44°C, pH 8 Solvents: 1, Steps: 1, Stages: 2
1.2 C:HCl, 2.5 h, 80°C
Transformation:
Uncategorized
Source
Preliminary research on allantoin
synthesis
Liu, Aiwen; Chen, Xin; Wu, Peiyi
Guangdong Huagong
Volume 29
Issue 2
Pages 26-28
Journal
2002
Sciences School
Foshan University
Foshan, Peop. Rep. China 528000
Number of Steps
1
92. Single Step

1 1.1 C:ZrO2, C:14808-79-8, 75 h, 2.5°C Reactants: 2, Catalysts: 2, Steps: 1, 62%
Stages: 1
Transformation:
Source
Synthesis of allantoin on solid
superacid catalyst
Xu, Wenyuan; Xia, Fei; Xiong,
Guoxuan
Huaxue Shijie
Volume 43
Issue 2
Pages 79-81
Journal
2002
Applied Chemistry Department
East China Geological Institute
Fuzhou, Peop. Rep. China 344000
Number of Steps
1
93. Single Step

1 1.1 C:H2SO4, S:H2O regioselective, catalyst on Duolite, other 52% (85:15) /
1.2 S:H2O catalysts gave lower yield, Reactants: 3,
Catalysts: 1, Solvents: 1, Steps: 1, 52% (85:15) /
Stages: 2
13%
Transformations:
1. Aminoalkylation and
Amidoalkylation of Aromatic
Compounds
Source
The use of solid acids to promote the
one-pot synthesis of DL-5-(4-
hydroxyphenyl)hydantoin
Applied Catalysis, A: General
Volume 224
Issue 1-2
Pages 153-159
Journal
2002
Departamento de Quimica Organica,
Instituto de Ciencia de Materiales de
Aragon
Universidad de Zaragoza C.S.I.C.
Number of Steps
1
94. Single Step

1 1.1 C:H2SO4, S:H2O regioselective, catalyst on Dowex, other 76% (85:15) /
1.2 S:H2O catalysts gave lower yield, Reactants: 3,
Catalysts: 1, Solvents: 1, Steps: 1, 76% (85:15) /
Stages: 2
16%
Transformations:
1. Aminoalkylation and
Amidoalkylation of Aromatic
Compounds
Source
The use of solid acids to promote the
one-pot synthesis of DL-5-(4-
hydroxyphenyl)hydantoin
Applied Catalysis, A: General
Volume 224
Issue 1-2
Pages 153-159
Journal
2002
Departamento de Quimica Organica,
Instituto de Ciencia de Materiales de
Aragon
Universidad de Zaragoza C.S.I.C.
Number of Steps
1
95. Single Step

1.1 R:HNO3, R:NaNO2, S:H2O 26%
Steps: 1, Stages: 3
1.2 R:CaCl2 Transformation:
1.3 R:HCl, S:H2O Uncategorized
Source
Process for synthesizing allantoin
He, Chuhua; He, Ying; He, Litao
2001
Patent Information
May 30, 2001
CN 1296946
A
Number of Steps
1
96. Single Step

1.1 R:HNO3, R:O2, R:NaNO2, S:H2O 27%
Steps: 1, Stages: 3
1.2 R:CaCl2 Transformation:
1.3
Uncategorized
Source
Process for synthesizing allantoin
He, Chuhua; He, Ying; He, Litao
2000
Patent Information
Nov 01, 2000
CN 1271728
A
Number of Steps
1
97. 2 Steps

1.1 R:NaOH, R:H2O2, S:H2O 80%
Steps: 1, Stages: 1
[Reactant]

2 2.1 C:14808-79-8, C:TiO2, S:H2O Reactants: 2, Catalysts: 2, Solvents: 1, 57%
Steps: 1, Stages: 1
Source
Synthesis of allantoin by solid
superacid SO42-/TiO2
Zhao, Jinglian; Zhang, Guohua
Riyong Huaxue Gongye
Volume 30
Issue 6
Pages 10-12
Journal
2000
Xi'an Jiaotong University
Number of Steps
2
98. Single Step

1 1.1 C:14808-79-8, C:TiO2, S:H2O Reactants: 2, Catalysts: 2, Solvents: 1, 57%
Steps: 1, Stages: 1
Transformation:
Source
Synthesis of allantoin by solid
superacid SO42-/TiO2
Zhao, Jinglian; Zhang, Guohua
Riyong Huaxue Gongye
Volume 30
Issue 6
Pages 10-12
Journal
2000
Xi'an Jiaotong University
Number of Steps
1
99. Single Step

1.1 R:HNO3, S:H2O 42%
Steps: 1, Stages: 2
1.2
Transformation:
Uncategorized
Source
Study on synthesis process of
allantoin
Zhang, Chuanmei
Henan Huagong
Issue 7
Pages 9-10
Journal
2000
Henan School of Chemical Industry
Zhengzhou, Peop. Rep. China
450042
Number of Steps
1
100. Single Step

1 ENZYMATIC REACTION, PHOSPHATE 49% / 32%
1.1 R:H2O2, S:H2O BUFFER USED, Reactants: 1,
Stages: 1
Transformation:
1. Hydrolysis or Hydrogenolysis of
Amides/ Imides/ Carbamates
Source
Further Insights into the
Electrooxidation of N-Methyluric Acids
and Correlation of Oxidation
Potentials with Frontier MO Energies
Goyal, Rajendra N.; Thankachan, P.
P.; Jain, Neena
Bulletin of the Chemical Society of
Japan
Volume 73
Issue 7
Pages 1515-1524
Journal
2000
Dep. Chem.
University of Roorkee
Roorkee, India 247667
Number of Steps
1
101. Single Step

1.1 R:KOH, R:KMnO4, S:H2O 26% / 14%
Steps: 1, Stages: 1
Transformation:
Uncategorized
Source
The mechanism for the conversion of
uric acid into uroxanate and allantoin.
A new base-induced 1,2-carboxylate
shift
Poje, M.; Sokolic-Maravic, Lea
Tetrahedron
Volume 44
Issue 21
Pages 6723-8
Journal
1988
Fac. Sci.
Univ. Zagreb
Zagreb, Yugoslavia 41001
Number of Steps
1
102. Single Step

1 Equimolar iodine, Reactants: 1,
1.1 R:LiOH, R:I2, S:H2O 70%
Stages: 2
1.2 R:AcOH
Transformation:
Uncategorized
Source
uric acid into allantoin and
dehydroallantoin. A new look at an
old problem
Tetrahedron
Volume 42
Issue 2
Pages 747-51
Journal
1986
Fac. Sci.
Univ. Zagreb
Number of Steps
1
103. Single Step

1 Excess iodine, Reactants: 1, Reagents:
1.1 R:LiOH, R:I2, S:H2O 4, Solvents: 1, Steps: 1, Stages: 3
1.2 R:Na2SO3 Transformation:
1.3 R:AcOH Uncategorized
Source
uric acid into allantoin and
dehydroallantoin. A new look at an
old problem
Tetrahedron
Volume 42
Issue 2
Pages 747-51
Journal
1986
Fac. Sci.
Univ. Zagreb
Number of Steps
1
104. Single Step

1 Reactants: 2, Steps: 1, Stages: 1
1.1
Transformation:
Source
Glycoluril identification in allantoin
Baloniak, Sylwester; Blaszczak,
Henryka
Acta Poloniae Pharmaceutica
Volume 40
Issue 2
Pages 249-50
Journal
1983
Inst. Chem.
Sch. Med.
Poznan, Pol. 60-780
Number of Steps
1
105. Single Step

1 Reactants: 2, Steps: 1, Stages: 1
1.1
Transformation:
Source
5-Ureidohydantoin
Assignee Permachem Asia, Ltd.,
Japan
1982
Patent Information
Mar 25, 1982
JP 57050969
A
Number of Steps
1
106. Single Step

1 Classification: Oxidative cleavage;
1.1 R:KMnO4, S:H2O Decarbonylation; Ring cleavage;
Isomerisation; # Conditions: KMnO4
NaOH; H2O 30 deg 20mn, Reactants: 1,
Stages: 1
Transformation:
Uncategorized
Source
New synthesis of uric acid and 1,7-
dimethyluric acid
Bills, C. Wayne; Gebura, Stanley E.;
Meek, John S.; Sweeting, Orville J.
Journal of Organic Chemistry
Volume 27
Pages 4633-5
Journal
1962
Univ. of Colorado
Boulder
Number of Steps
1
107. Single Step

1 Classification: Ring cleavage;
1.1 R:AcOH 75%
Hydrolysis; Decarboxylation; #
Conditions: AcOH; # Comments: also
Org. Synth., 13, 1; yield 65-75%;
reactant is a potassium salt; reactant not
isolated, Reactants: 1, Reagents: 1,
Steps: 1, Stages: 1
Transformation:
1. Decarboxylation of Aliphatic Acids
Source
2-Amino-4-nitrophenol
Hartman, W. W.; Silloway, H. L.
Organic Syntheses
Volume 25
Pages 5-7
Journal
1945
Number of Steps
1
108. 2 Steps

1 NaOH, H2O, 80 C, KMnO4, 30 C/15
1.1 R:NaOH, R:KMnO4, S:H2O min., Oxidation, Rearrangement,
Steps: 1, Stages: 1

2 AcOH, Decarboxylation, Ring cleavage,
2.1 R:AcOH Reactants: 1, Reagents: 1, Steps: 1,
Stages: 1
Source
Allantoin
Hartman, W. W.; Moffett, E. W.;
Dickey, J. B.
Organic Syntheses
Volume 13
Pages 1-3
Journal
1933
Number of Steps
2
109. Single Step

1 NaOH, H2O, 80 C, KMnO4, 30 C/15
1.1 R:NaOH, R:AcOH, R:KMnO4, S:H2O, S:AcOH 45%
min., AcOH, Ring cleavage, Ring
contraction, Reactants: 1, Reagents: 3,
Transformation:
Uncategorized
Source
Allantoin
Dickey, J. B.
Organic Syntheses
Volume 13
Pages 1-3
Journal
1933
Number of Steps
1
110. Single Step

1 AcOH, Decarboxylation, Ring cleavage,
1.1 R:AcOH Reactants: 1, Reagents: 1, Steps: 1,
Stages: 1
Transformation:
1. Decarboxylation of Aliphatic Acids
Source
Allantoin
Dickey, J. B.
Organic Syntheses
Volume 13
Pages 1-3
Journal
1933
Number of Steps
1
111. Single Step

1 Classification: Ring cleavage;
1.1 R:H2O, S:H2O 67%
Hydrolysis; # Conditions: H2O Rf 2h; #
Comments: other examples, Reactants:
1, Reagents: 1, Solvents: 1, Steps: 1,
Stages: 1
Transformation:
1. Dealkoxylation of Acetals,
Orthoesters and Ethers
Source
Allantoin and its methyl derivatives
Biltz, H.; Max, F.
Berichte der Deutschen Chemischen
Gesellschaft [Abteilung] B:
Abhandlungen
Volume 54B
Pages 2451-76
Journal
1921
Number of Steps
1

Alantoina

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1.2 R:HCl, S:H2O, pH 4

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