CS262590B1 - 3-amine-4-hydroxy-/n-phenyl/-benzensulphamide and process for preparing thereof - Google Patents

Abstract

3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide Formula I is prepared by reaction of aniline in an alkaline acetate medium with 2-nitrochlorobenzene-4-sulfochloride and hydrolysis of the resulting 3-nitro-4-chloro- - (N-phenyl) -benzenesulfamide in alkaline temperature at 3-nitro- -4-Hydroxy- (N-phenyl) -benzenesulfonamide, from which the resulting reduction is obtained by iron reduction product.

Description

The invention relates to 3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide and to a process for its preparation.

For dyeing wool and polyamide in weakly acid to neutral baths, metal-complex dyes are used, where 2-amino-phenol-4-sulfamide and its alkyl derivatives are used as active components. The compound 3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide has now been prepared, which has a commercial application.

A process for the preparation of 3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide of the formula

OH

consists in reacting aniline in acetate with 2-nitrochlorobenzene-4-sulfochloride to give 3-nitro-4-chloro- (N-phenyl) -benzenesulfamide, which is brought to an elevated temperature of 3- nitro-4-hydroxy- (N-phenyl) -benzenesulfamide from which the resulting product is obtained by reduction with iron.

The preparation of 3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide is illustrated by the following example.

Example

137 parts of crystalline sodium acetate are introduced into 500 parts of water. After dissolution, 93 parts of aniline are introduced and 256 parts of 2-nitrochlorobenzene-4-sulfochloride are introduced within 5 minutes thereafter. Heat to 58 ° C and stir for 4 hours, maintaining the pH in the range of 4.5 to 7. The resulting 3-nitro-4-chloro (N-phenyl) -benzenesulfamide is filtered off with suction, washed with 250 parts of water until reaction to chloride disappears. ions. 14 parts of sodium hydroxide are dissolved in 118 parts of water. 31.2 parts of 3-nitro-4-chloro- (N-phenyl) -benzenesulfamide are cured at 100C, heated to 100C and heated for 5 hours. When the Beilstein reaction is a negative halogen reaction, 0.2 parts of carboraffin is added, the solution is filtered and 20 parts by volume of 50% sulfuric acid are added dropwise to the filtrate. The resulting 3-nitro-4-hydroxy- (N-phenyl, benzenesulfamide) was filtered off with suction and washed with water until neutral, 82 parts of iron filings were introduced into 750 parts of water, heated to 80 ° C, 6 parts of acetic acid were added. The mixture was boiled and boiled for 20 minutes, then 54 parts of 3-nitro-4-hydroxy- (N-phenyl) -benzenesulfamide were added over 2 hours and heated to boiling for a further 2 hours. of anhydrous soda which had previously dissolved in 50 parts of water After disappearing the reaction to ferric ions, 10 parts of sodium hydroxide dissolved in 30 parts of water were added and filtered hot, 1 part of Na 2 SO 4 was added to the filtrate and left under nitrogen. After cooling to 5-10 ° C, the filtrates are neutralized with stirring by adding 25 volumes of 35% BC1 to neutral reaction to pH 7. The precipitated 3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide is filtered off with suction, washed with 20 ml. The yield was 42.9 parts (88.5% of theory) e, gray product, mp 174-175 ° C.

Claims (2)

A 3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide of the formula 2. A process for the preparation of 3-amino-4-hydroxy- (N-phenyl) -benzenesulfamide according to claim 1, wherein the aniline is reacted with 2-nitrochlorobenzene-4-sulfo chloride to form 3-nitro-4 in an alkaline acetate medium. -chloro- (N-phenyl) -benzenesulfamide, converted by hydrolysis in an alkaline medium above room temperature to 3-nitro-4-hydroxy- (N-phenyl) -benzenesulfamide, from which the resulting product is obtained by reduction with iron.