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Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione

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Chemistry of Heterocyclic Compounds Aims and scope

Alkylation of 1,3-dihydro-2Н-benzimidazole-2-thione (2-mercaptobenzimidazole) with bromoethane and chloroacetic acid derivatives occurrs at the sulfur atom, leading to the corresponding 2-sulfanylbenz-imidazole derivatives. Aminomethylation of 1,3-dihydro-2Н-benzimidazole-2-thione with piperidine and 4-methylpiperidine gives reaction products at both nitrogen atoms, while reaction with morpholine gives derivative at only one nitrogen atom, which is in an equilibrium with the starting compound and bis-adduct in DMSO solution.

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This work received financial support from the Russian Science Foundation (grant No. 14-13-00126). The experiments were performed by using equipment at the Saint Petersburg State University Resource Centers "Center for Magnetic Resonance Research", "Center for X-ray Diffraction Studies", "Center for Chemical Analysis and Material Research".

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Correspondence to M. A. Kuznetsov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1684–1696, November, 2014.

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Bespalov, A.Y., Gorchakova, T.L., Ivanov, A.Y. et al. Alkylation and Aminomethylation of 1,3-Dihydro-2Н-Benzimidazole-2-Thione. Chem Heterocycl Comp 50, 1547–1558 (2015).

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