SU445272A1 - Process for preparing sulfamide derivatives - Google Patents

Abstract

Method for producing sulphamide derivatives of general formula NH? 1 it-HN $ OgSOgl ^ HR2K, NCH2CH2S02SO ^ CH ^ CH ^ NRiKg

Description

where R, E is alkyl, substituted alkyl, for example -CH2CH250 C H, Y is OH, OCHj, COOH, C 1, H, characterized by the fact that where Y has the indicated values, and the resulting product is then treated in an alkaline medium with dialkylamine, o, N- carbonyl-1-amino-8-naphthol-3, 6-disulfonyl chloride is subjected to amidation with a water-soluble amine of the general formula HgCHgOSOsH where R, R2 have the indicated meanings, followed by isolation of the target product in a known manner.

The invention relates to a process for the preparation of new compounds that can be used for the synthesis of active dyes.

There is a general method for the preparation of arylsulfamides, which consists in

action of a concentrated ammonia solution on arylsulfonyl chloride.

A process for the preparation of sulfamide derivatives of the general formula is described.

HNSOe

R l iNCHgCHgSOz

OHNH2

$ OOS

sogCH CH miRj where R, El - alkyls, substituted alkyls, for example -CHjCHjSOjHi Y - OH, OCHj, COOH, C1, H is that 0, N-Ka NILE-1-amino-8-naphthol-3 The 6-disulfonyl chloride acts as a water-soluble aromatic amine of the general formula SOgCHgCHjOSO H 1 where they have the indicated Values, followed by treatment of the product with dialkylamines where H, B2 have the indicated values in an alkaline medium and release the desired product in a known manner. Example. A. Amidirovanie. To a solution of 9.38 g of 99.3% A- / J-hydroxyethylsulfonyl-2-aminoanisole sulfate ester (mol. Weight 311) in 100 ml of water and 35 ml of 8% sodium bicarbonate solution (pH 6.5 ) add a suspension of 4.55 g of 95% O, N-carbonyl-1-amino-8-naphthol-3, 6 disulfonyl chloride, prepared in a known manner, in 25 ml of water and 0.3 ml of pyridine. The reaction mass is stirred for 3 hours at room temperature, perederiva pH 5-6.5 by the addition of 8% sodium bicarbonate solution. At the end of the reaction, hydrochloric acid is added to pH 4.0, then 20 g of potassium chloride are added and the mixture is placed at room temperature for 2 hours. The precipitate formed is dried. 7 g of 0, N-carbonyl {1-amino-8-naphthol-3, 6-bis (2-methoxy5 jb sulfoxyethylsulfonylphenyl) sulphamidase; concentration on sulfoether groups 77.3%, yield 78.5%.

CHgCHgOSOjH

osnz

§02WH-

S02

SNGNGO OZN

To confirm the structure of the obtained product, 1-acetylamino-8-naphthol-3,6-bis- {(2methoxy-5-hydroxyethylsulfonylphenyl) sulfamid3 (mp 233-235 ° C with decomposition) was synthesized by alkaline hydrolysis of i1 followed by acetylation of the amino group

3

axes

H1Tog $ - 5AoA§bzln. CHjCH oH

 .0 Found,%: C 44.21, 44.31) H 4.47, 4; 60; N 4.90, 5.05 "S 15.81,

16.11- ..

Calculated,%: C 44.72; H 4.35, N 5.22i S 15.90.

B. To a solution of 12 g of 77.3% O, N-carbonyl-1-amino-8-naphthol 3, 6-bis C (2-methoxy-5- (Y sulfonic ethyl sulfonyl phenyl) sulfamide J in 100 ml of water is added 12 , 8 g of 65% methyl taurine, a solution of raz445272 HE INSOS3

CH2CH20N

stir for 1 hour while maintaining pH 9 with 20% sodium hydroxide solution. The reaction mixture is cooled, acidified with chemically pure hydrochloric acid to pH 6, the supernatant separated and stirred with 100 ml of ice water, filtered and dried at room temperature.

13 g of 1-amino-8-naphthol 3,6-bis- (2-methoxy-5- (-Y-methyl-Ysulfoethylaminoethyl) gsulfonylphenyl sulfamide J, amine concentration 75%, yield 96% are obtained.

SO NHso cHgCH H-af,

en2SY2 $ charge

3-1-amino-8-naphthol-3, 6-bis-2-methoxy-5 - ((i- -K-methyl-N-sulfoethylaminoethylsulfonyl) -phenylsulfamide was synthesized from a 1S-acetylamino-8-naphthol 3, 6 -bis- (2-methoxy-5- (3-hydroxy-40 ethylsulfonylphenyl) -sulfamide}, ideally obtained according to item A.

OSSN

 SNGNG OzN sye

Compounds of the formula G are obtained in a similar manner with the following values: S02CH2CH2NR R2 and Y

5-892: CH2CH2H (CH3) 2, 2-OCH ,;

4-S02CH2CH2N (CHj) CH2CH2SOaH j H

4-S02CH CH N (CiH5) z; H; - 2-och.

5-S02CH2CH N (02%), i (CH352;

Claims (1)

A method of producing sulfamide derivatives of the general formula where 1C, I ^ -alkyls, substituted alkyls, for example ~ CH2CH2S0 ₃ H, Y — OH, OCHj, COOH, C1, H, revealing that where Y has the indicated meanings, and the resulting product is then treated in alkaline medium with dialkylamine NH ^ Rj, O, Y-carbonyl-1-amino-8-naphthol-3,6-disulfochloride is subjected to amidation with a water-soluble amine · general formula S0 _z CH _z CH ₂ 0 SO ₃ H where Rp It, - have the indicated meanings, followed by isolation of the target product in a known manner.