Open Access Open Access  Restricted Access Subscription Access

METHYLATION OF 5-NITROTETRAZOLE SODIUM SALT UNDER PHASE-TRANSFER CATALYSIS CONDITIONS

Юлия Н. Павлюкова, Ольга М. Нестерова, Михаил А. Илюшин, Владимир А. Островский
Cover Image

Abstract


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.

Authors: Yulia N. Pavlyukova, Olga M. Nesterova, Mikhail A. Ilyushin, Vladimir A. Ostrovskii*

 


Keywords


1-methyl-5-nitrotetrazole; 2-methyl-5-nitrotetrazole; 5-nitrotetrazole sodium salt; tetrabutylammonium bromide; alkylation; phase-transfer catalysis; two-phase water – organic solvent mixtures

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv