Synthesis of 1,3,5-triazine-2-thiol derivatives on the basis of N-perchloroethenylbenzimidoyl chloride and its analogs

Reactions of N-perchloroethenylbenzimidoyl chloride and its analogs with th iourea do not yield the expected 6-aryl-4-dichloromethyl-1,3,5-triazine-2-t hiols since the initial imidoylation occurs at the sulfur rather than nitro gen atom of thiourea. Nevertheless, condensation of the above difunctional electrophilic reagents, N-perchloroethenylbenzimidoyl chloride and its anal ogs, with S-alkylisothiuronium iodides leads to formation of 4,6-disubstitu ted 2-alkylthio-1,3,5-triazines in high yields. Their N-alkyl isomers were synthesized by successive treatment of N-perchloroethenylbenzirnidoyl chlor ides with highly basic primary amines and sodium thiocyanate.