New route for preparation of nitrosubstituted 1,2-phenylenediamines

Authors

  • MaroŠ Bella,

    1. Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského street 9, 812 37 Bratislava, Slovak Republic
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  • Viktor Milata

    1. Department of Organic Chemistry, Institute of Organic Chemistry, Catalysis and Petrochemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského street 9, 812 37 Bratislava, Slovak Republic
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  • Dedicated to Prof. Miha Tišler on the occasion of his 80th birthday

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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