Dichloromethane → HCID 86608217, compound

Participants

Reaction Conditions

Reaction Steps

A commercially available 34% methylene chloride solution of ethyl azidoacetate (6.6 mL, 21.6 mmol) was concentrated in vacuo, the residue reconstituted in anhydrous ethanol (100 mL) and the resulting solution treated with 3-(4-bromophenyl)-3H-imidazole-4-carbaldehyde (6) (2.7 g, 10.8 mmol). The mixture was cooled to 0° C., treated dropwise with potassium ethoxide solution (5.1 mL, 13.0 mmol, 24% (w/w) EtOH solution) and the mixture stirred at 0° C. for 5 h. The resulting white solid was collected by filtration and dried in air to yield ethyl 2-azido-3-[3-(4-bromophenyl)-3H-imidazol-4-yl]acrylate (7). LC-MS (ES+): m/z 362/364 (1/1) [MH+]. 1H NMR (CDCl3, 400 MHz): δ=1.31 (t, J=7.1 Hz, 3H), 4.30 (q, J=7.1 Hz, 2H), 6.52 (d, J=0.7 Hz, 1H), 7.19 (d, J=8.7 Hz, 2H), 7.67 (s, 1H), 7.68 (d, J=8.7 Hz, 2H), 8.03 (d, J=0.7 Hz, 1H).

Provenance & Evidence