The Reaction of β-Cyanoethylhydrazine with Diethyl Phenylthiocarbamoylmalonate
2014
Mohamed Sallam, Mohamed Mohamed | Elnagdi, Mohamed Helmy | Fleita, Daizy Hanna | Hartmann, Eric
Diethyl phenylthiocarbamoylmalonate (2) reacts with β-cyanoethylhydrazin (1) to yield ethyl 3-anilino-2-pyrazolin-5-one (3) via decyanoethylation of the reaction intermediates.Whereas 2 reacts with hydrazine hydrate in refluxing ethanol to yield a mixture of 3-anilino-2-pyrazolin-5-one (4) and the hydrazide (5), the diethyl ester (6) is formed on treatment of 2 with the same reagent in a cooled ethanolic solution. On the other hand, 2 reacts with hydrazine hydrate in the absence of a solvent to yield the carboxylic acid (7).Benzoylacetonitrile reacts with phenylisothiocyanate to yield the thioanilide (8). The latter compound neither reacts with hydrazine hydrate not β-cyanoethylhydrazine.
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