Benzaldehyde → HCID 178518082, compound

Participants

Reaction Steps

The numbers in the formula are aimed for characterizing NMR-spectra. To a solution of benzaldehyde (1 equiv., 0.85 mmol, 94 μL) and benzylisocyanide (1 equiv., 0.85 mmol, 92 μL) in methanol (0.6 mL) was added KOCN (1 equiv., 0.85 mmol, 68 mg) in H2O (0.3 mL) followed by 4-chloroaniline (1 equiv., 0.85 mmol, 98 mg) and pyridinium hydrochloride (1 equiv., 0.85 mmol). The reaction was stirred at room temperature for 3 days and the precipitate filtered. Work-up and purification afforded (rac)-4-benzylamino-1-(4-chloro-phenyl)-5-phenyl-1,5-dihydro-imidazol-2-one (117 mg, 37%) as an amber solid. δH NMR (CDCl3, 300 MHz) 7.45-7.10 (14H, m, H arom), 5.54 (1H, s, C5H), 5.35 (1H, br signal, NH), 4.71 (1H, dd, J=14.5, 5.6 Hz, CHAHBPh), 4.52 (1H, dd, J=14.5, 4.1 Hz, CHAHBPh); m/z (EI) 378.3 (37%), 377.3 (26), 376.3 (100, M+H+).

Provenance & Evidence