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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.

european chemical bulletin

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