Triethylamine → N-Methyl-N-methoxy-2-(1-triphenylmethyl-1H-imidazol-4-yl)acetamide

Participants

Reaction Steps

To a solution of 4-imidazoleacetic acid (1.04 g, 6.40 mmol) and triphenylmethyl bromide (2.48 g, 7.68 mmol) in dimethylformamide (40 ml) was added triethylamine (4.46 ml, 32 mmol) and the suspension allowed to stir for 18 hours at room temperature. After this time, the mixture was treated with 3-hydroxy-1,2,3-benzotriazin-4(3)-one (HOOBT) (1.31 g, 8 mmol), N, O-dimethylhydroxyamine hydrochloride (1.56 g, 16 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (1.53 g, 8 mmol) and stirred for 24 hours at room temperature. After this time, sat. aq. sodium bicarbonate (50 ml) and water (50 ml) were added and the mixture was extracted with ethyl acetate (2×100 ml). The combined extracts were washed with sat. aq. NaHCO3 (100 ml) and then brine (50 ml) and the solvent evaporated in vacuo. The residue was suspended in ether (20 ml) and the white solid filtered to give the title compound as a white solid. 1NMR(CD3OD, 300 MHz) δ 7.37(10H, m), 7.16(6H, m), 6.84(1H, s), 3.73(2H, s), 3.68(3H, s) and 3.18(3H, s)ppm.

Provenance & Evidence