GB726789A - Triphenylmethane derivatives - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0726789/IV (b)/1> wherein Y and Z stand for hydrogen, halogen, alkyl, alkoxy, amino or acylamino and m and n are integers. Preferably Y and/or Z are chlorine atoms, a preferred product being the compound of the formula <FORM:0726789/IV (b)/2> The compounds are made by reacting 2 : 21-dihydroxy triphenylmethanes of the general formula <FORM:0726789/IV (b)/3> with a dihalogenomethane, preferably at an elevated temperature, e.g. at about 100 DEG C., in a closed vessel. When the initial products are salts they may be converted to the free acid by treatment with a strong acid. Amine products may be acylated if desired. The products may also be made by first forming a product free from sulphonic groups and subsequently sulphonating. Corresponding ethers in which the methylene group is replaced by longer alkylene chains may be similarly prepared. In examples: (1) 2 : 2-dihydroxy-3 : 5 : 31 : 51 : 411-pentachlorotriphenylmethane-211-sulphonic acid is treated with methylene chloride to give 2 : 21-methylenedioxy - 3 : 5 : 31 : 51 : 411 - pentachloro - triphenylmethane-211-sulphonic acid; (2) 2 : 2-dihydroxy - 3 : 5 : 31 : 51 : 411 - pentachloro - triphenylmethane is treated with methylene dibromide and the product is sulphonated to give 2 : 21 - methylenedioxy - 3 : 5 : 31 : 51 : 411-pentachloro - triphenylmethane - 311 - sulphonic acid; (3) 2 : 21 - dihydroxy - 3 : 5 : 31 : 51 - tetrachloro - triphenylmethane - 211 - sulphonic acid is treated as in (1) to give the 2 : 21-methylenedioxy compound; (4) 2 : 21 - dihydroxy - 5 : 51 : 411 - trichloro - triphenylmethane-211-sulphonic acid is reacted with methylene dichloride to give the 2 : 21-methylenedioxy compound; (5) 2 : 21-dihydroxy-3 : 5 : 31 : 51-tetrachloro - 411 - amino - triphenylmethane - 211-sulphonic acid is treated as in (4) to give the 2 : 21 - methylenedioxy compound; (6) the product of (5) is acetylated to the corresponding acetylamine compound; (7) 2 : 21-dihydroxy-3 : 31 - dimethyl - 5 : 51 : 411 - trichloro - triphenylmethane-211-sulphonic acid is treated with methylene dichloride to give the 2 : 21 - methylenedioxy p compound; (8) 2 : 21 - dihydroxy - 3 : 5 : 6 : 31 : 51 : 61 : 411 - heptachloro - triphenylmethane - 211 - sulphonic acid is converted to the methylene ether; and (9) 2 : 21-dihydroxy - 3 : 5 : 31 : 51 - tetrachloro - 411 - methoxy triphenylmethane is treated with methylene dichloride and sulphonated to give 2 : 21 - methylenedioxy - 3 : 5 : 31 : 51 - tetrachloro - 411 - methoxy - triphenylmethane - 311 - sulphonic acid; the sulphonic acid starting materials and products of these examples being generally in the form of their sodium salts. Specifications 316,900, 330,893, 337,808, 338,126, [all in Class 2 (iii)], and 422,923 are referred to.