GB749908A - Manufacture of xanthenium compounds - Google Patents

Abstract

Asymmetrical xanthenium compounds of the formula:-<FORM:0749908/IV(c)/1> where X is halogen or alkoxy, R1 is hydrogen, or an aliphatic or cycloaliphatic radical and R2 is an aromatic radical, in which the benzene nucleus carrying the sulphonic acid radical may contain further substituents, are made by reacting at up to 100 DEG C. in a solvent containing hydroxyl groups, preferably in the molecular proportion of 1:1, a primary or secondary amine other than a diarylamine with an intermediate of the formula:- <FORM:0749908/IV(c)/2> where X is halogen or alkoxy and nucleus A may be substituted. These intermediates may be made by condensing benze 2 - sulpho - 1 - carboxylic acids with resorcinol in presence of phosphorus oxyhalides or from resorcinol sulphophthalein by replacing the hydroxy groups para to the central carbon atom by halogen atoms or alkoxy groups. In examples, the internal salt of 3.6 - dichloro - 9 - phenyl - xanthhydrol - 21 - sulphonic acid is condensed in methanol, or glycol, so as to replace one chlorine atom only, with the following amines, (1) aniline, (2) p - anisidine, (3) p - nitraniline, (4) 2 - nitro - 4 - toluidine, (5) 1 - amino - 2 - methoxylbenzene - 5 - sulphonic acid diethylamide, (6) p - amino - acetanilide, (7) 3 - amino - N - ethyl - carbazole (8) p - aminophenyl - b - hydroxyethyl sulphone, (9) 3 - amino - 4 - methoxyphenyl - b hydroxyethyl sulphone, (10) 4 - amino - 3, 5 - dimethylphenyl - b - hydroxyethyl sulphone, (11) 1 - amino - 2 - hydroxy - 3 - benzoic acid, (12) 1 - amino - 2.6 - dimethylbenzene, (13) 1 - methylamino - 2.5 - dimethyl - benzene, (14) 1 - amino - 2 - methyl - 6 - chlorobenzene, (15) 1 - amino - 2 - trifluoromethylbenzene, (16) 1 - amino - 2 - methyl - 4 - cyclohexylbenzene, (17) 4 - amino - 3.21 - dimethyl - azobenzene, (18) 1 - (41 - aminophenyl) - 3 - methyl - 5 - pyrazolone, (19) sodium dehydrothio - p - toluidine sulphonate, (20) ammonium 4 - amino - diphenylamine - 2 - sulphonate, (21) sodium 1 - aminobenzene - 3 - sulphonate, (22) sodium 1 - amino - 2 - hydroxy - 5 - sulpho - 3 - benzoate, (23) 1 - ethylamino - 2 - methylbenzene, (24) butylaminobenzene, (25) ethylaminobenzene. Also in examples, (26) the internal salt of 3.6 dichloro - 9 - phenyl - xanthhydrol - 21.41 - disulphonic acid is condensed with aniline, 1 - methylamino - 2 - methylbenzene, or mesidine, (27) the internal salt of 3.6 - dichloro - 9 - phenyl - xanthhydrol - 41 - methoxy - 21 - sulphonic acid is condensed with p - toluidine, (28) the internal salt of 3.6 - dichlor - 9 - phenyl - xanthhydrol - 41 - carboxy - 21 - sulphonic acid is condensed with p - phenetidine, and (29) the internal salt of 3.6.41 - trichloro - 9 - phenyl - xanthhydrol - 21 - sulphonic acid is condensed with ethylaminobenzene or sodium 4 - aminodiphenyl ether - 2 - sulphonate. Other starting materials are specified. Specification 744,972 is referred to.