Reactions of 2-aminobenzothiazoles with ethylene chlorohydrin, molecular and crystal structure of bis[(3-β-hydroxyethyl)benzothiazolyl-2-endene]ammonium chloride

Article abstract of DOI:10.1007/BF01164719

Hydroxyethylation of 2-aminobenzothiazoles by ethylene chlorohydrin unexpectedly led to preferential formation of 3-β-chloroethylbenzothiazolin-2-one. In the case of unsubstituted 2-aminobenzothiazole, we also isolated the target 2-imino-3-β-hydroxyethylbenzothiazoline and bis[(3-β-hydroxyethyl)benzothiazolyl-2-indene]ammonium chloride. As a result of reaction of 2-aminobenzothiazole with 3-β-chloroethylbenzothiazolin-2-one, we obtained 2-(benzothiazolyl-2-imino)-3-[β-(2-oxobenzothiazolin-3-yl)ethyl] benzothiazoline. The structure of the synthesized compounds was established based on x-ray diffraction, PMR, IR, UV, and mass spectra. 1997 Plenum Publishing Corporation.