Aromatic and heterocyclic nitriles react with N-methylhydroxylamine to give N-hydroxy-N-methylamidines (4). The latter, when treated with ethyl chloroformate, give 1,2,4-oxadiazol-5(2H)-ones (9). Sodium borohydride reduces compound (9; R =p-C6H4Cl) to the corresponding oxadiazolidinone (10). The tautomeric structure of p-chlorobenzamide oxime is discussed.
P. W. Seale and W. K. Warburton, J. Chem. Soc., Perkin Trans. 1, 1974, 85 DOI: 10.1039/P19740000085
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