2-naphtylamine-6-sulfonyl aniline and its prepn and application

CN 1349981 A
Abstract
The present invention relates to a compound 2-naphthylamine-6-sulfonylaniline, its preparation
method and use. Its preparation method includes the following steps: making Bronner's acid and
acetic anhydride produce reaction to obtain acetyl Bronner's acid, then making dried acetyl
Bronner's acid, chlorosulfonic acid and sulfoxide chloride produce reaction, then making said
obtained material undergo the processes of ice liberation and water-washing to obtain sulfonyl
chloride compound of acetyl Bronner's acid, then making said compound react with aniline,
through the processes of hydrolysis and neutralization, to obtain the invented product which can
be used as intermediate of dyestuff.
Claims(3) translated from Chinese
Compound 2-naphthylamine -6- anilide 1. A name, having the formula: Image not available.
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2. The compound of claim 1, wherein 2-naphthylamine -6- anilide as dye intermediates.
A compound of the 2-naphthylamine -6- anilide of claim 3. A method for preparing, wherein: the
drying acetyl Bron acid with chlorosulfonic acid, thionyl chloride by 1:2.8-3.1 :0.8-10 weight
ratio of the feed, the reaction was stirred at 45-50 , and then analyze the ice, water, and the
resulting acetyl Bron acid chloride compound in pH = 11 ~ 12 reacted with aniline, by
hydrolysis, and that is to get product.
Description translated from Chinese
2-naphthylamine 6-sulfonyl aniline and preparation and use

TECHNICAL FIELD The present invention relates to a novel naphthylamine anilide compounds
and preparation method and use, specifically, the compound 2-naphthylamine -6- anilide of a
name, and the process for preparing the compound purposes.

The purpose of the invention to create content of this invention is to provide a name of the
compound 2-naphthylamine 6-sulfonyl aniline, preparation and use of the compound, the
compound can be used as dye intermediates, synthetic method is simple, clean, high yield, good
product quality.

Specific technical solutions are as follows: Compound 2-naphthylamine -6- anilide of a name,
having the formula: Image not available. View PDF The melting point of this compound 218-
220 , can be used as dye intermediates.

A method of 2-naphthylamine -6- sulfonanilides prepared: it is the acetyl acid and chlorine
Bulong acid, thionyl chloride effect analysis by ice, washing Bron acids derived acetyl chloride
compounds, After reaction with aniline, and then by hydrolysis, and to obtain the product. The
reaction for preparing the compound of the formula: Image not available. View PDF According
to the present invention, when synthesized by the acetyl Bron acid: chlorosulfonic acid: thionyl
chloride = 1:2.8-3.1:0.8-1.0 (weight ratio) the addition the mixture was stirred at 45-50 2h,
Then ice-out, washed with water, and the resulting intermediate in the pH = 11 ~ 12 under the
action of aniline, then pH = 14,95-98 hydrolyzed 2h, cooled to 50 , neutralized with
hydrochloric acid until neutral, was cooled to precipitate product, filtered, washed twice to obtain
qualified products.
According to the present invention, the acetyl Bulong acid under alkaline conditions, Bulong
acid and acetic anhydride stirred 1.5h at 85-90 , direct drying derived.

In the acetylation reaction of this step, strict control of the amount of water, after the completion
of the reaction, vacuum drying, thereby increasing the yield, to avoid waste, chlorosulfonated is
the key, the feed ratio by acetyl Bron acid: chlorosulfonic acid: chlorine of sulfoxide = 1:2.8-
3.1:0.8-1.0 (weight ratio), up to the purpose of the present invention.

Using techniques of the present invention, in which the acetylation reaction step without brown-
black water, to avoid environmental pollution, the yield is close to 100%, and can meet the
quality requirements of the subsequent reaction, greatly reduce production costs and improve the
economic efficiency; in chlorosulfonation reaction, strictly control the acetyl Bulong acid:
chlorosulfonic acid: the ratio of thionyl chloride, and its product quality to meet export
requirements.

Compounds of the present invention, the melting point of 218-220 , the product was analyzed
by HPLC, content greater than 98%, the total yield of 94%, with good prospects and the outlook
for exports.

In three 100mL flask of water, NaOH7g, Bulong acid 30g, acetic anhydride 16g, 85-90 under
stirring 1.5h, vacuum drying acetyl Bulong acid.

In another three-necked flask was added chlorosulfonic acid 31g, dry acetyl Bron acid 10.5g,
thionyl chloride 9g, stirred at 45-50 2h, then poured into 120g of ice water, add 130g of ice-
water, ice precipitation, filtration , the product was washed with ice water until pH = 4-5.

The wet product into the above-mentioned three-neck flask, water 70mL, adjusted with 50%
NaOH pH = 12, 7g freshly distilled aniline was added, the reaction at 20-25 2h, adding a base
to maintain constant pH = 12, then 50 % NaOH 14g, 95-98 hydrolysis 2h, cooled to 50 ,
with 36% hydrochloric pH = 7. The precipitated product is cooled, filtered, washed twice
qualified products have an overall yield of 94%, by PHLC analyze content of> 98%.

Example 2 250ml three-necked flask, water 35ml, NaOH 2.2g, and stirred to dissolve Houjiarubu
Long acid 10g, acetic anhydride 5.5g, warmed to dissolve 70 , 80 ~ 90 reaction was stirred
for 1 hour, poured into evaporator, infrared lamp drying to constant weight in acetyl Bulong acid
12.70g, yield 98.6%.

In 100ml three-necked flask was added chlorosulfonic acid 28g (reaction is carried out in a
hood), dried added with stirring acetyl Bron acid 10g, together with thionyl chloride 8g, 45
2 The reaction was stirred for 1.5 hours at 0.5 hours , then poured with stirring into 120g of water
and 120g of ice, the precipitated bright yellow product, vacuum filtration, washed with ice to pH
= 5 ~ 6.

The above-described wet product in a 250ml three-necked flask, water 60ml, mixed into a paste,
NaOH30% solution was added dropwise to pH = 11 ~ 12, the dropwise addition of freshly
distilled aniline 6.5g, After the addition was stirred at room temperature 1.5 hours, pH value will
continue to decline, should resupply NaOH, to maintain the pH = 11 ~ 12, and then added 30%
NaOH20g, 93 ~ 100 reaction was stirred for 2 hours, cooled to 40 , adjusted with 18% HCl
pH6 ~ 7, the precipitated product was cooled, filtered under reduced pressure, washed twice with
water, with a total yield of about 94%. HPLC analysis: content of 98%.