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

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 r...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2017-06, Vol.53 (6-7), p.733-736
Main Authors: Pavlyukova, Yulia N., Nesterova, Olga M., Ilyushin, Mikhail A., Ostrovskii, Vladimir A.
Format: Article
Language:English
Subjects:
Alkylation
Catalysis
Chemical industry
Chemistry
Chemistry and Materials Science
Dichloromethane
Dimethyl sulfate
Methylation
Organic Chemistry
Pharmacy
Phase transfer catalysts
Sodium
Tetrabutylammonium bromide
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-017-2118-5