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N-chloro-N-benzoiloxy benzamide

Svetlana V. Kravchenko

Abstract


N-Chloro-N-(benzoyloxy)benzamide has been synthesized by chlorination of N-benzoyloxybenzamide with tert-butylhypochlorite. The structure of N-chloro-N-(benzoyloxy)benzamide has been соnfirmed by its NMR 1H and mass-spectra. Upon storage at −26 °C, the labile N-chloro-N-(benzoyloxy)benzamide quickly converts into N-(benzoyloxy)benzamide. Reaction of N-chloro-N-(benzoyloxy)benzamide with anhydrous sodium acetate in acetonitrile gives N-benzoyloxybenzamide. 4-N,N-Dimethylaminopyridine reacts with N-chloro-N-(benzoyloxy)benzamide in acetonitrile leading to 4-N,N-dimethylaminopyridine hydrochloride and N-benzoyloxybenzamide. In both cases, the  products of nucleophilic substitution at the amide nitrogen have not been found. The N-Cl bond polarization  in N-chloro-N-(benzoyloxy)benzamide disfavors nucleophilic substitution at the amide nitrogen. Investigation of the interactions of N-chloro-N-(benzoyloxy)benzamide with AcONa and 4-N,N-dimethylaminopyridine  has shown that nucleophilic substitution at the nitrogen atom does not occur in the case of N-chloro-N-acyloxyamides.  

Keywords


N-chloro-N-acyloxybenzamides; N-acyloxybenzamides; nucleophilic substitution at nitrogen atom

References


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DOI: http://dx.doi.org/10.15421/081307

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