Collect. Czech. Chem. Commun. 1980, 45, 1065-1071

Hydrolysis kinetics and mechanism of N'-(3-N-methylcarbamoyloxyphenyl)-N,N-dimethylformamidine

Alexandr Čegan, Jaroslav Šlosar and Miroslav Večeřa

Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice


Hydrolysis of N' -(3-N-methylcarbamoyloxyphenyl)-N,N-dimethylformamidine (I) has been studied in mixture water-dioxane (4 : 1) at pH 1 to 13. The hydrolysis rates of methylcarbamoyl and dimethylformamidine groups are comparable within pH range 4 to 10, and they differ by as much as several orders of magnitude in pH ranges 1-3 and 11-13. The hydrolysis products of the whole pH range have been determined by paper chromatography, and reaction mechanism has been suggested on the basis of the measured hydrolysis rate constants.Effects of protonation and hydratation of dimethylformamidine group on the hydrolysis rate of the methylcarbamoyl group is discussed.