Maurice Fleury Bernard, S. Letellier, J. Porziemsky
1986
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Journal
Analyst
Abstract
The behaviour of 2-{[(2-amino-5-chlorophenyl)phenylmethylene]amino}acetamide in aqueous solution was investigated in the pH range 1.0–8.0, with respect to the E or Z configuration around the imine bond. The E isomer yields kinetic data that obey the kinetic law for successive first-order reactions. The first step consists of the isometric transformation of the E to the Z isomer. The second step implies a parallel reaction mechanism, i.e., either a hydrolysis yielding 2-amino-5-chlorobenzophenone or an intramolecular ring closure reaction yielding desmethyldiazepam. This parallel route constitutes a major reaction at pH values below the pKa of the immonium-imine equilibrium, as demonstrated by UV spectrophotometry and high performance liquid chromatography.