Journal article

Reaction of 2-(4'-thiazolyl)benzimidazole (thiabendazole) with alkyl halides

JA Maynard, ID Rae, D Rash, JM Swan

Australian Journal of Chemistry | Published : 1971


2-(4?-Thiazolyl)benzimidazole (thiabendazole) is alkylated at a benzimidazole nitrogen by reaction with sodium hydride and an alkyl halide. With 1,3-dibromo-propane and 1,2-dibromoethane, the thiazole nitrogen is also alkylated to give quaternary salts containing the 6,7- dihydro-5H-thiazolo[3?,4?:1.2][1,4]diazepino-[8,9-a]benzimidazole and 5,6-dihydrothiazolo[3?,4?:1,2]pyrazino[7,8-a]benzimidazole ring systems respectively. The structures proposed for these tetracyclic products are supported by spectroscopic examination of the products formed by alkali fission of their thiazole rings.

University of Melbourne Researchers

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