A base induced fragmentation of tetramisole

The exposure of dl‐2,3,5,6‐tetrahydro‐6‐phenylimidazo[2,1‐6 Jthiazole (tetramisole) to lithium diisopropylamide in tetrahydrofuran ruptures the thiazole ring to give, following the introduction of primary or secondary alkyl halides, 1‐(2′‐alkylthio)ethyl‐4‐phenylimidazoles. Conclusive evidence for the thiazole ring opening was obtained by a single crystal x‐ray diffraction study of 1‐(2′‐p‐bromobenzylthio)ethyl‐4‐phenylimidazole.