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Modification of 2-trifluoromethyl-1H-benzimidazole with hydroxyalkyl substituents

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Abstract

Alkylation of 2-(trifluoromethyl)-1H-benzimidazole with 4-bromobutyl acetate gave 4-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]butyl acetate which was deacylated by the action of hydrogen chloride in anhydrous ethanol. 4-[2-(Trifluoromethyl)-1H-benzimidazol-1-yl]butan-1-ol thus formed showed a moderate tuberculostatic activity. Alkylation of the title compound with chloromethyloxirane afforded a mixture of 1-chloro-3-[2-(trifluoromethyl)-1H-benzimidazol-1-yl]-propan-2-ol and 1-(oxiran-2-ylmethyl)-2-trifluoromethyl-1H-benzimidazole. A new procedure was proposed for the synthesis of 2-[(2-trifluoromethyl-1Hbenzimidazol-1-yl)methoxy]ethyl acetate.

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990, Russia

    E. V. Shchegol’kov, A. E. Ivanova, Ya. V. Burgart, V. I. Saloutin & O. N. Chupakhin

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  1. E. V. Shchegol’kov
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  2. A. E. Ivanova
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  3. Ya. V. Burgart
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  4. V. I. Saloutin
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  5. O. N. Chupakhin
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Correspondence to A. E. Ivanova.

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Dedicated to Full Member of the Russian Academy of Sciences I.P. Beletskaya on her jubilee

Original Russian Text © E.V. Shchegol’kov, A.E. Ivanova, Ya.V. Burgart, V.I. Saloutin, O.N. Chupakhin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 3, pp. 429–432.

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Shchegol’kov, E.V., Ivanova, A.E., Burgart, Y.V. et al. Modification of 2-trifluoromethyl-1H-benzimidazole with hydroxyalkyl substituents. Russ J Org Chem 49, 417–420 (2013). https://doi.org/10.1134/S1070428013030172

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  • DOI: https://doi.org/10.1134/S1070428013030172

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