Syntheses of Arylsulfone-thiazole Derivatives. III

Synthesis of 2-Amino-4-methyl (or phenyl)-5-p-aminobenzenesulfone-thiazole

Abstract

2-Amino-4-phenyl-5-p-aminobenzenesulfone-thiazole was obtained by the condensation of ω-bromo-ω-p-acetaminobenzenesulfone-acetophenone and thiourea and subsequent hydrolysis. Bromination of p-acetaminobenzenesulfone-acetone in NaOH solution results in the substitution of Br in methylene radical situated between sulfone and carbonyl radicals. When this is condensed with thiourea and then hydrolyzed, 2-amino-4-methyl-5-p-aminobenzenesulfone-thiazole (methylpromizole) is obtained. Halogenation, if made in glacial AcOH solution, results in substitution of halogen atom in the methylene radical at the end so that, when this is condensed with thiourea and subsequently hydrolyzed, 2-amino-4-p-aminobenzenesulfone-methylthiazole is obtained.