Abstract
Oxidation of 1-methyl-1H-imidazole-2-thiol with chlorine dioxide was performed for the first time, and the results were shown to depend on the oxidation conditions. Optimal conditions were found for the preparation of 1-methylimidazole-2-sulfonic acid, 2,2′-disulfanediylbis(1-methylimidazole) hydrochlorite, and 1-methyl-3-sulfo-3H-imidazolium chloride. A new salt, 4-methylanilinium 1-methyl-1H-imidazole-2-sulfonate, was isolated.
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Loginova, I.V., Chukicheva, I.Yu., and Kuchin, A.V., Russ. J. Org. Chem., 2011, vol. 47, p. 1501.
Loginova, I.V., Rodygin, K.S., Rubtsova, S.A., Slepukhin, P.A., Kuchin, A.V., and Polukeev, V.A., Russ. J. Org. Chem., 2011, vol. 47, p. 124.
Kuchin, A.V., Rubtsova, S.A., Karmanova, L.P., Subbotina, S.N., and Loginova, I.V., Izv. Akad. Nauk, Ser. Khim., 1998, p. 2110.
Kuchin, A.V., Rubtsova, S.A., and Loginova, I.V., Izv. Akad. Nauk, Ser. Khim., 2001, p. 413.
Kuchin, A.V., Rubtsova, S.A., Loginova, I.V., and Subbotina, S.N., Russ. J. Org. Chem., 2000, vol. 36, p. 1819.
Loginova, I.V., Ashikhmina, E.V., Rubtsova, S.A., Krymskaya, Yu.V., and Kuchin, A.V., Russ. J. Org. Chem., 2008, vol. 44, p. 1773.
Sudarikov, D.V., Kuropatov, V.A., Rubtsova, S.A., Cherkasov, V.K., and Kuchin, A.V., Izv. Vyssh. Uchebn. Zaved., Ser. Khim. Khim. Tekhnol., 2008, vol. 51, no. 10, p. 112.
Lezina, O.M., Rubtsova, S.A., and Kuchin, A.V., Izv. Akad. Nauk, Ser. Khim., 2003, p. 1779.
Lezina, O.M., Rubtsova, S.A., and Kuchin, A.V., Russian Patent no. 2 302 407, 2006; Byull. Izobret., 2007, no. 19.
Lezina, O.M., Rubtsova, S.A., and Kuchin, A.V., Russ. J. Org. Chem., 2011, vol. 47, 1249.
Belikov, V.G., Sinteticheskie i prirodnye lekarstvennye sredstva (Synthetic and Natural Medicines), Moscow: Vysshaya Shkola, 1993, p. 315.
Gilchrist, T.L., Heterocyclic Chemistry, Harlow, Essex, England: Longman Scientific & Technical, 1992, 2nd ed. Translated under the title Khimiya geterotsiklicheskikh soedinenii, Moscow: Mir, 1996, p. 9.
Shtefan, E.D. and Vvedenskii, V.Yu., Usp. Khim., 1996, vol. 65, p. 326.
Duus, F., Comprehensive Organic Chemistry, Barton, D. and Ollis, W.D., Eds., Oxford: Pergamon, 1979, vol. 3. Translated under the title Obshchaya organicheskaya khimiya, Moscow: Khimiya, 1983, vol. 5, p. 594.
Handoo, K.L., Handoo, S.K., Gadru, K., and Kaul, A., Tetrahedron Lett., 1985, vol. 26, p. 1765.
Aragoni, M.C., Arca, M., Demartin, F., Devillanova, F.A., Garau, A., Isaia, F., Lippolis, V., and Verani, G., J. Am. Chem. Soc., 2002, vol. 124, p. 4538.
Nikitin, I.I., Khimiya kislorodnykh soedinenii galogenov (Chemistry of Oxygen Compounds of Halogens), Moscow: Nauka, 1986.
Yakupov, M.Z., Shishlov, N.M., Shereshovets, V.V., and Imashev, U.B., Neftekhimiya, 2001, vol. 41, p. 52.
Methoden der organischen Chemie (Houben-Weyl), Müller, E., Bayer, O., Meerwein, H., and Ziegler, K., Eds., Stuttgart: Georg Thieme, 1953, 4th ed., vol. 2. Translated under the title Metody organicheskoi khimii, Moscow: Khimiya, 1967, vol. 2, p. 610.
Zolfigol, M.A., Khazaei, A., Moosavi-Zare, A.R., Zare, A., and Khakyzadeh, V., Appl. Catal. A: General, 2011, vol. 400, p. 70.
CrysAlis CCD, version 1.171.29.9 (release 23-03-2006 CrysAlis171.NET), Oxford Diffraction.
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.
Tumanova, T.A. and Flis, I.E., Fiziko-khimicheskie osnovy otbelki (Physicochemical Principles of Bleaching), Moscow: Lesnaya Promyshlennost’, 1972, p. 236.
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Dedicated to Full Member of the Russian Academy of Sciences G.A. Tolstikov on his 80th anniversary
Original Russian Text © O.M. Lezina, S.A. Rubtsova, D.V. Belykh, P.A. Slepukhin, A.V. Kutchin, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 1, pp. 117–123.
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Lezina, O.M., Rubtsova, S.A., Belykh, D.V. et al. Oxidation of 1-methyl-1H-imidazole-2-thiol with chlorine dioxide. Russ J Org Chem 49, 112–118 (2013). https://doi.org/10.1134/S1070428013010193
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DOI: https://doi.org/10.1134/S1070428013010193