Collect. Czech. Chem. Commun. 1987, 52, 1006-1014

The synthesis and reactions of trisubstituted N-(X-2-benzothiazolyl)formamidines

Margita Lácová and Nguyen Thi Nga

Department of Organic Chemistry, Comenius University, 842 15 Bratislava


The modified Vilsmeier-Haack reagent ANC(O)H-ClSO2C6H5 (A = (CH3)2, (C2H5)2, (CH2)5, CH2CH2OCH2CH2) reacts with 2-amino-X-benzothiazole in pyridine and ether to give three types of products in high yields depending on the character of substituents A and X. Isolated were: N,N-dialkyl-N'-(X-2-benzothiazolyl)formamidines, N,N'-bis(X-2-benzothiazolyl)formamidines, and N,N-dialkyl-N',N´´-bis(X-2-benzothiazolyl)triaminomethanes. Investigated were the conditions and reaction products of N,N-dialkyl-N',N´´-bis(X-2-benzothiazolyl)triaminomethanes with phenylethanoyl, phenoxyethanoyl, 4-chlorophenoxyethanoyl, and N-phthalimidoethanoyl chlorides either in ether or in pyridine. Mutual transformations of the individual products are described.