Ammonia → HCID 13019464, compound

Participants

Reaction Steps

A solution of (E) and (Z)-N,N-dimethyl-3-(4-methoxyphenyl)-3-[(1-phenylmethyl)imidazol-2-yl]-2-propen-1-amine (1.0 g) in dry toluene (20 ml) was added to liquid ammonia (20 ml) with stirring at -78°. Sodium was added until the mixture was deep blue (ca. 0.23 g required). After stirring at -78° for 2 h. ammonium chloride (1 g) was added, the mixture allowed to warm to room temperature and the residue partitioned between 2 N sodium carbonate (50 ml) and ethyl acetate (3×50 ml). The organic solution was dried (Na2SO4) and concentrated to give the title compound as a white solid (0.67 g) which crystallised from ether with m.p. 131°-133°, ωmax (CHBr3) 3440 (NH), 2770, 2820 (Me2NCH2 --).

Provenance & Evidence