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The nitration and bromination of 2-(pentafluorosulfanyl)-1,3-benzothiazole and 2-(trifluoromethyl)-1,3-benzothiazole

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Chemistry of Heterocyclic Compounds Aims and scope

The nitration and halogenation reactions of 2-(pentafluorosulfanyl)- and 2-(trifluoromethyl)-1,3-benzothiazoles were studied. Methods for the preparation of previously undescribed mononitro-substituted 1,3-benzothiazoles (4-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole, 4-nitro-2-(trifluoromethyl)-1,3-benzothiazole, and 6-nitro-2-(pentafluorosulfanyl)-1,3-benzothiazole) as well as a new method for the synthesis of the previously known 6-nitro-2-(trifluoromethyl)-1,3-benzothiazole were developed. The procedure involved the reaction of 2-(trifluoromethyl)-1,3-benzothiazole with NH4NO3 in TFAA at room temperature. An efficient method for the preparation of 2-substituted 4,5,6,7-tetrabromo-1,3-benzothiazoles based on the reaction of 2-substituted 1,3-benzothiazoles with NBS in TFA–H2SO4 at room temperature was proposed.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv, 02660, Ukraine

    Olexandr I. Guzyr, Lyudmila M. Potikha & Yuriy G. Shermolovich

  2. Kyiv Taras Shevchenko National University, 64 Volodymyrska St., Kyiv, 01033, Ukraine

    Lyudmila M. Potikha

  3. State Scientific Institution “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv, 61001, Ukraine

    Svitlana V. Shishkina

  4. Life Chemicals Inc., 1A Dixie Ave., Niagara-on-the-Lake, ON, L0S, 1J0, Canada

    Volodymyr N. Fetyukhin

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  1. Olexandr I. Guzyr
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Correspondence to Olexandr I. Guzyr.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 304–308

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Guzyr, O.I., Potikha, L.M., Shishkina, S.V. et al. The nitration and bromination of 2-(pentafluorosulfanyl)-1,3-benzothiazole and 2-(trifluoromethyl)-1,3-benzothiazole. Chem Heterocycl Comp 59, 304–308 (2023). https://doi.org/10.1007/s10593-023-03197-9

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