Tert-Butyl nitrite → Ethyl 1-phenylimidazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

Tert-butyl nitrite (535 mg, 5.19 mmol) in dry dimethylformamide (15 ml) was heated to 65° C. under nitrogen and then 1-(4-aminophenyl)imidazole-4-carboxylic acid ethyl ester (see part (ii)) (800 mg, 3.463 mmol) in dry dimethylformamide (5 ml) was added over 10 minutes. The mixture was heated at 65° C. for a further 20 minutes and then cooled to room temperature. The mixture was poured into saturated brine (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with dichloromethane gave the title compound (520 mg, 70%) as an off-white solid.

Provenance & Evidence