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2H-benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles

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Neugebauer,  Franz A.
Department of Organic Chemistry, Max Planck Institute for Medical Research, Max Planck Society;

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Citation

Iddon, B., Kutschy, P., Robinson, A. G., Suschitzky, H., Kramer, W., & Neugebauer, F. A. (1992). 2H-benzimidazoles (isobenzimidazoles). Part 7. A new route to triclabendazole [5-chloro-6-(2,3-dichlorophenoxy)-2-methylthio-1H-benzimidazole] and congeneric benzimidazoles. Journal of the Chemical Society, Perkin Transactions 1, 22: 2/03252J, pp. 3129-3134. doi:10.1039/P19920003129.


Cite as: https://hdl.handle.net/11858/00-001M-0000-0019-ABB6-F
Abstract
A new synthesis of the selective anthelmintic agent triclabendazole 7 from the readily available 5,6-dichloro-2H-benzimidazole-2-spirocyclohexane 2 by simple steps is described. Analogous benzi-midazoles difficult to prepare by conventional methods are similarly obtained. Triclabendazole can exist as a low-melting metastable solid (m.p. 85–90 °C) convertible by heating or recrystallisation from ethanol into its stable form (m.p. 176–178 °C).