Hydrolysis of ureas. Kinetics and mechanism of the basic hydrolysis of indole-1-carboxamides and (5H-dibenz[b,f]azepine)-5-carboxamide

The hydroxide ion catalyzed hydrolysis of indole-1-carboxamide and indole-1-(N,N-dimethyl)carboxamide has been studied in water at 60.0° and [OH⁻] concentration between 0.3--2.4N. The rate constants of formation of the tetrahedral intermediate are strongly increased by N-substitution with a heteroaromatic ring in comparison with simple amides. Carbamazepine, (5H-dibenz[b,f]azepine)-5-carboxamide, a potent anticonvulsant drug, is particularly stable under these conditions.