A new synthesis of tetramisole hydrochloride, (°)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1- b]thiazole hydrochloride

Abstract

Tetramisole hydrochloride, a potent anthelmintic, has now been synthesized by condensation of styrene oxide and ethylenimine. The product, 1-(P-hydroxy-phenethyl)aziridine, reacts with thiourea or thiocyanic acid to yield 3-(P-hydroxy-phenethyl)-2-iminothiazolidine. Following chlorination with thionyl chloride, a base-catalysed cyclization gives tetramisole. The method provides a general route to 2,3,5,6-tetrahydroimidazo[2,l-b]thiazoles.