A ring-fission/C–C bond cleavage reaction with an N-alkyl-N-methyl-N-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]amine

The reaction of N-(3,4-dichlorophenethyl)-N-methylamine () with 3-chloromethyl-5-phenyl-1,2,4-oxadiazole () was investigated. Employment of an equimolar amount of and in the presence of potassium carbonate led to the expected tertiary amine (N-[(3,4-dichlorophenyl)ethyl]-N-methyl-N-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]amine), whereas an excess of and prolonged reaction time resulted in ring fission of the oxadiazole system in and finally in the formation of N′-benzoyl-N-[(3,4-dichlorophenyl)ethyl]-N-methylguanidine () and N,N′-bis[(3,4-dichlorophenyl)ethyl]-N,N′-dimethylmethanediamine (). The structures of products were determined by means of 1H and 13C NMR-spectroscopy, mass spectrometry and IR-spectroscopy, for (as picrate) and also X-ray structure analysis was employed. A possible mechanism of the reaction pathway leading to compounds and is proposed.