Formaldehyde → 1-(2,4-Dichlorophenylmethyl)-4,5-dihydro-2-(1-phenylethenyl)imidazole

Participants

Reaction Steps

1-(2,4-Dichlorophenyl)methyl-4,5-dihydro-2-phenylmethylimidazole (3.19 g, 0.1 mol) was added to a slurry of sodium hydride (80% dispersion in mineral oil, 0.3 g, 0.01 mol) in dry dimethylformamide (15 ml) and the mixture was stirred at room temperature for 30 minutes. Paraformaldehyde (3 g, 0.01 mol) was added to the reaction mixture and the resulting mixture was heated at 70° C. for 6 hours. The reaction mixture was cooled, water was added and the resulting mixture was extracted with ether. The organic phase was separated, washed with brine, dried over anhydrous magnesium sulphate, and concentrated under reduced pressure. The resulting residue was chromatographed on silica gel in ammonia/methanol/ethyl acetate (1:4:45) to yield 1-(2,4-dichlorophenylmethyl)-4,5-dihydro-2-(1-phenylethenyl)imidazole (2.6 g), (δ (CDC13) 3.3 (2H, t,J=6 Hz), 3.95 (2H, t,J=6 Hz), 4.1 (2H,s), 5.65 (1H, s), 5.8 (1H, s), and 7.0-7.5 (8H, m) p.p.m. having the formula ##STR25##

Provenance & Evidence