Patent GB-474423-A (GB)
Title: Process for the manufacture of sulphonic acid amide compounds
IPC: C07C311/37
Filed: 1936-04-28
Abstract: Acylaminobenzene-sulphonamides are prepared by acylating an aminobenzene-sulphonamide, in which a sulphonamide group is present in p-position to the amino group or in which two sulphonamide groups are present in any position, with unsubstituted aliphatic or araliphatic monocarboxylic acids containing at least 5 carbon atoms or derivatives thereof, such as halides, esters, anhydrides or azides.  If the sulphonamide groups are substituted, they may only contain unsubstituted alkyl, aralkyl or cycloalkyl radicles.  In an alternative method, acylaminobenzenes which contain a substituent, such as a sulphonic ester or halide group, in the appropriate position or positions and in which the acyl group is derived from a monocarboxylic acid as above specified, are treated with ammonia or a simple amine to convert the said substituent into the sulphonamide group.  The products possess therapeutic properties.  According to the examples: (1) 4-aminobenzene-sulphonamide is treated with oleyl methyl ester to give the 4-oleylamino compound; (2) the acylation of 4-aminobenzene-sulphonamide is effected by means of the acid chlorides of caproic, caprylic, capric, lauric, myristic, palmitic, stearic, undecylenic, erucic, behenolic and phenylacetic acids; similarly, using lauric acid chloride, the following aminosulphonamides, viz.: aminobenzene-3 : 5-di-(sulphonic acid dimethylamide) and 4-aminobenzene-sulphonic acid benzylamide, butylamide and piperidide, are converted into the corresponding 4-lauroylamino compounds; (3) 4-aminobenzene is acylated with valeric acid chloride and cinnamic acid azide, and 4-amino-benzene-sulphonic acid diethylamide by means of cinnamic acid azide; (4) 4-amino-3 : 6-dimethoxybenzene-sulphonamide, 4-amino-3 : 6-dimethylbenzene - sulphonamide, 4 - amino-3-methylbenzene - sulphonamide, 4 - amino - 2-methylbenzene - sulphonamide, 4 - amino - 3-methoxy - 6 - methylbenzene - sulphonamide and 2 - methyl - 4 - amino - 5 - chlorobenzene - sulphonamide are treated with oleic acid chloride, and 4-amino-3-methoxy-6-methylbenzene-sulphonamide with isovaleric acid chloride; (5) 4-aminobenzene-sulphonic acid is treated first with isovaleric acid chloride and then with phosphorus pentachloride and the product reacted with ammonia or cyclohexylamine in methyl alcoholic solution to give 4-isovaleroylaminobenzene-sulphonic acid amide and cyclohexylamide respectively.  The Provisional Specification states that the processes of the invention are also applicable to the preparation of acylamino compounds derived from such cyclic sulphonamide compounds as have at least in part an aromatic character.  4 - Amino - 3 : 6 - dimethylbenzene - sulphonamide is obtained by reacting 4-acetylamino-3 : 6 - dimethylbenzene - sulphochloride with ammonia and saponifying. 4-Amino-3-methoxy-6-methyl- and 2-methyl-4-amino-5-chloro-benzene-sulphonamides are prepared in a similar manner to the 3 : 6-dimethyl compound.  4-Amino-2 and 3-methylbenzene-sulphonamides are obtained by treating 4-acetylamino-2 and 3-methylbenzene-sulphonic acids first with phosphorus pentachloride and then with ammonia.