Patent GB-470461-A (GB)
Title: Process for the manufacture of cyclic aminosulphonic acid amide compounds
IPC: C07C311/37
Filed: 1936-02-11
Abstract: Aminosulphonic acid amides of the benzene series are made by acylating the amino group attached to the nucleus of an aminosulphonic acid amide of the benzene series which contains a sulphonamide group in p-position to the said amino group attached to the nucleus or which contains two sulphonamide groups attached to the nucleus by the action of cyanic acid or by an acylating agent which is substituted by a hydroxyl or amino group or by an alkylated, aralkylated, cycloalkylated, arylated, or acylated hydroxyl or amino group.  Alternatively, a p-acylamino-benzenesulphonamide or an acylaminobenzene-disulphonamide containing a halogen atom in the acyl radicle is (a) hydrolyzed to give the hydroxy compound or (b) treated with the metallate of a hydroxyl compound to give an ether, or (c) treated with ammonia or an alkylamine, aralkylamine, cycloalkylamine, arylamine or an acid amide to give the corresponding amino compound, or (d) where the acyl radicle contains a nitro group instead of the halogen atom, is reduced to the amino body.  Also, a hydroxyacyl- or amino-acylamino-benzene p- (or di-)-sulphonic acid ester or halide, which may be substituted in the hydroxyl or amino group by an alkyl, aralkyl, cyclo-alkyl, aryl or acyl group is reacted with ammonia or amines. In the products, the hydrogen atoms of the sulphonamide group or groups may be wholly or partially substituted by alkyl, aralkyl or cycloalkyl radicles, or two hydrogen atoms may be replaced by an alkylene radicle, and the hydrogen atom of the substituted amino group attached to the nucleus may also be replaced by alkyl, aralkyl, cycloalkyl, or aryl.  As acyl radicles are specified radicles of aromatic and aliphatic carboxylic and sulphonic acids, and the hydroxy- and aminoacyl radicles may contain alkyl, aralkyl, cycloalkyl, aryl or acyl substituents.  In examples, the hydrochloride of 4-aminobenzenesulphonamide is condensed with (1) butoxyacetic anhydride to give butoxyacetylaminobenzene-4-sulphonamide; (2) methoxyacetic anhydride; (3) ethoxy-acetic acid chloride; (4) 2<1>-chlorophenoxy-acetyl chloride; (5) phenoxyacetyl chloride; (6) 2-isopropyl-5-methylphenoxyacetic ethyl ester; (7) phenoxypropylsulphonic acid chloride; (8) 3<1>-nitrobenzoyl chloride (followed by reduction); (9) 3<1>.5<1>-dinitrobenzoyl chloride (followed by reduction); (10) 3<1>-nitrobenzenesulphonyl chloride (followed by reduction); (11) diethylamino-acetic ester; (12) chloracetyl chloride followed by replacement of the chlorine by reaction with (a) ammonia, (b) butylamine, (c) ethylamine, (d) propylamine, (e) allylamine, (f) piperidine, (g) diethylamine; (13) b -chlorpropionyl chloride, followed by reaction with butylamine; (14) diethyl-bromo-acetyl chloride, followed by reaction with butylamine to give butylaminoisocaproylaminobenzene - 4 - sulphonic acid amide; (15) chlor-acetyl chloride, followed by boiling with sodium acetate solution to give the hydroxy compound; (16) lactic acid; (17) acetoacetic acid ethyl ester to give b -hydroxycrotonylaminobenzene - 4 - sulphonamide; (18) chloroformic acid ethyl ester to give carbethoxyaminobenzene-4-sulphonamide; (19) potassium cyanate to give ureidobenzene-4-sulphonamide.  Also in examples, ethoxyacetyl chloride is reacted with (20) aminobenzene-4-sulphonic acid diethylamide; (21) aminobenzene-4-sulphonic acid benzylamide; (22) aminobenzene-4-sulphonic acid piperidide; and (23) aminobenzene-3.5-di-(sulphonic acid dimethylamide); (24) methoxy acetyl chloride is reacted with diphenylamine-4-sulphonamide; (25) phenoxypropylsulphonyl chloride is reacted with 2-methoxy-5-methyl-1-aminobenzene-4-sulphonamide.  Also, chloracetyl chloride is reacted with each of the following compounds, followed by reaction with butylamine; (26) aminobenzene-4-sulphonic acid butylamide; (27) aminobenzene-4-sulphonic acid hydroxyethylamide; (28) aminobenzene-4-sulphonic acid benzylamide; (29) 2-ethoxy-5-methyl-1-chloracetylaminobenzene - 4 - sulphonamide; (30) chloracetylaminobenzene-3.5-disulphonic acid dimethylamide. Finally, (31) ethoxyacetylaminobenzene-4-sulphonic acid (obtained from ethoxyacetylchloride and aminobenzene-4-sulphonic acid) is converted to its sulphochloride and the latter reacted with ammonia or cyclohexylamine.  Diphenylamine-4-sulphonamide is obtained from chlorsulphonic acid and diphenylamine, and treating the diphenylamine - 4 - sulphochloride so obtained with ammonia.  Phenoxypropyl sulphonic acid chloride is prepared by reacting phenoxypropyl bromide with sodium sulphite, and treating the sulphonic acid with phosphorus pentachloride.  Specification 430,580 is referred to.