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New route for preparation of nitrosubstituted 1,2-phenylenediamines

✍ Scribed by MaroŠ Bella; Viktor Milata

Publisher
Journal of Heterocyclic Chemistry
Year
2008
Tongue
English
Weight
206 KB
Volume
45
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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4‐Nitrobenzoselenadiazole was methylated with dimethylsulphate to give corresponding 1‐N‐methyl‐4‐nitrobenzoselenadiazolium methylsulphate which after alkaline ring‐opening afforded 1‐N‐methyl‐3‐nitro‐1,2‐phenylenediamine in 90% yield. This compound was also prepared from 3‐nitro‐1,2‐phenylenediamine by monomethylation through tosylation, methylation and detosylation and was confirmed and characterised as 1‐methyl‐4‐nitrobenzimidazole. Methylation of 5‐nitrobenzoselenadiazole and subsequent alkaline ring‐opening led to unseparable mixture of both methylated products.

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