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Methylation of 5-nitrotetrazole sodium salt under phase-transfer catalysis conditions

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Chemistry of Heterocyclic Compounds Aims and scope

The alkylation of 5-nitrotetrazole sodium salt with dimethyl sulfate was studied in a two-phase water–dichloromethane system in the presence of tetrabutylammonium bromide as a phase-transfer catalyst. The reaction produced a mixture of regioisomers – 1-methyl- and 2-methyl-5-nitrotetrazoles in 1:3 ratio. 2-Methyl-5-nitrotetrazole was obtained from this mixture as individual compound in 52% yield. The application of phase-transfer catalysis allowed to obtain 5-nitrotetrazole N-alkyl derivatives under conditions that did not require preliminary isolation of highly impact and friction sensitive 5-nitrotetrazole salts from aqueous solutions.

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The work was performed with financial support from the Russian Foundation for Basic Research (project RFFI No.17-0300566)

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Authors and Affiliations

  1. Saint Petersburg State Institute of Technology (Technical University), 26 Moskovsky Ave., Saint Petersburg, 190013, Russia

    Yulia N. Pavlyukova, Olga M. Nesterova, Mikhail A. Ilyushin & Vladimir A. Ostrovskii

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  1. Yulia N. Pavlyukova
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  2. Olga M. Nesterova
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  3. Mikhail A. Ilyushin
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  4. Vladimir A. Ostrovskii
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Correspondence to Vladimir A. Ostrovskii.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(6/7), 733–736

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Pavlyukova, Y.N., Nesterova, O.M., Ilyushin, M.A. et al. Methylation of 5-nitrotetrazole sodium salt under phase-transfer catalysis conditions. Chem Heterocycl Comp 53, 733–736 (2017). https://doi.org/10.1007/s10593-017-2118-5

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  • DOI: https://doi.org/10.1007/s10593-017-2118-5

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