DECARBAMOYLATION OF N-ALKOXY-N-(4-DIMETHYLAMINOPYRIDIN-1-IUM-1-YL)UREAS CHLORIDES IN DIMETHYLSULFOXIDE AS ROUTE TO 1-ALKOXYAMINO-4-DIMETHYLAMINOPYRIDINIUM CHLORIDES

Vasiliy Georgievich Shtamburg, Victor Vasilievich Shtamburg, Andrey Alexandrovich Anishchenko, Svetlana Vladimirovna Kravchenko, Alexander Vladimirovich Mazepa, Evgeniy Alexandrovich Klots

Abstract


Decarbamoylation of N-alkoxy-N-(4-dimethylaminopyridin-1-ium-1-yl)ureas chlorides in dimethylsulfoxide takes place with forming of 1-alkoxyaminopyridinium chlorides. N-Alkoxy substituent’s nature affects on ease of the decarbamoylation. Decarbamoylation of N-n-butyloxy-N-(4-dimethylaminopyridin-1-ium-1-yl)urea chloride at 20 ºC occurs with the selective forming of 1-n-butyloxyamino-4-dimethylaminopyridinium chloride. N-Methoxy-N-(4-dimethylaminopyridin-1-ium-1-yl)urea chloride is stable in dimethylsulfoxide at 20 ºC, but it forms selectively 1-methoxyamino-4-dimethylaminopyridium at 82 ºC heating during 1 hour. N-Ethoxy-N-(4-dimethylaminopyridin-1-ium-1-yl)urea chloride is also stable in dimethylsulfoxide at 20 ºC, but it converts in 1-ethoxyamino-4-dimethylaminopyridinium chloride at 100 ºC heating during 3 hour.

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DOI: http://dx.doi.org/10.17628/ecb.2018.7.267-271

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