Patent GB-326226-A (GB)
Title: Process for the manufacture of aromatic amino sulphochlorides substituted in the amino group
IPC: C07C309/86
Filed: 1928-11-30
Abstract: 326,226. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). Nov. 30, 1928. Aromatic aminosulphochlorides are manufactured by causing chlorsulphonic acid to act on an aromatic aminosulphonic acid substituted in the amino-group, or a nuclear substitution product thereof. According to the working conditions and the constitution of the aromatic aminosulphonic acid employed, either the corresponding aminosulphochloride is obtained or further sulphochloride residues are introduced into the molecule. The new compounds may be employed as intermediate products in the manufacture of dyestuffs, as therapeutic agents, as insecticides and in facilitating dyeing. The following compounds are specified :- from 2-acetylamino-5-naphthol-7-sulphonic acid, the 2 - acetylamino-5-naphthol-7- sulphochloride; from 2-acetylamino-8-naphthol-6- sulphonic acid the 2-acetylamino-8-naphthol-6- sulphochloride; from 1-acetylnaphthylamin-4-sulphonic acid the 1-acetylnaphthylamine-4-sulphochloride; from 1-acetylamino-8-naphthol-3 : 6-disulphonic acid the 1-acetylamino-8-naphthol-3 : 6 disulphochloride; from 1-acetylamino-8-naphthol- 4 : 6 - disulphonic acid the 1 - acetylamino-8- naphthol-4:6-disulphochloride; from 1-benzoylnaphthylamine-6-sulphonic acid the 1-benzoylnaphthylamine-6-sulphochloride; from carbonyl- 2 : 1-aminophenol-4-sulphonic acid the carbonyl- 2. 1-aminophenol - 4-sulphochloride; from carbonyl-2 : 1-aminophenol-4 : 6-disulphonic acid the carbonyl-2 : 1-aminophenol-4: 6-disulphochloride; from carbonyl - 1 : 2 aminonaphthol-4-sulphonic acid a carbonyl 1 - : 2-aminonaphtholdisulphochloride; from carbonyl-1 : 8-aminonaphthol-3 : 6- disulphonic acid the carbonyl-1 : 8-aminonaphthol- 3 : 6-disulphochloride; from 2-methyl benzoxazole- 5-sulphonic the corresponding monosulphochloride; from 2-hydroxy perimidine-5 :8-disulphonic acid the corresponding disulphochloride ; from 2-methylperimidine-6-sulphonic acid a disulphochloride; from diphenylurea-4 : 41-disulphonic acid the diphenylurea-4 : 4'disulphochloride; from 2-methylamino-1-methylbenzene-4-sulphonic acid the 2. methylamino - 1 - methylbenzene-4-sulphochloride; from dimethylaniline-3-sulphonic acid the dimethylaniline-3-sulphochloride; from 2-dimethylnaphthylamine-5-sulphonic acid two isomeric monosulphochlorides; from the diazoxydacid derived from 1-amino-2-naphthol-4-sulphonic acid, a diazoxydsulphochloride. Sulphonic acids. - 1-Benzoylnaphthylamine-6- sulphonic acid is obtained by the action of benzoylchloride on 1-naphthylamine-6-sulphonic acid. Carbonyl - 2 : 1-aminophenol-4 : 6-disulphonic acid is prepared by the action of phosgene on an alkaline solution of 2 : 1-aminophenol-4 : 6-disulphonic acid. In a. similar manner are obtained :-Carbonyl-1 : 2-aminonaphthol-4-sulphonic acid from 1 : 2-aminonaphthol-4-sulphonic acid, carbonyl-1 : 8-aminonaphthol-3 : 6-disulphonic acid from 1 : 8- aminonaphthol-3 : 6-disulphonic acid, 2-hydroxyperimidine-5 : 8-disulphonic acid from 1 : 8-naphthylenediamine-3 : 6-disulphonic acid, and diphenylurea-4 : 4<1>-disulphonic acid from aniline-4- sulphonic acid. 2-Methyl-benzoxazole-5-sulphonic acid is obtained by the action of acetic anhydride on 2 : 1-aminophenol-4-sodium sulphona.te, and in an analagous manner. 2 -methylperimidine-6-sulphonic acid from 1 : 8-naphthylenediamine-4-sulphonic acid. 2-Dimethylnaphthylamine - 5 - sulphonic acid is obtained by methylating 2-naphthylamine-5-sulphonic acid.