Triethylamine → N-methoxy-N,1-dimethyl-1H-imidazole-5-carboxamide

Participants

Reaction Steps

Triethylamine (5.51 mL, 39.646 mmol) was added slowly to a mixture of 1-methyl-1H-imidazole-5-carboxylic acid (2 g, 15.86 mmol), N,O-dimethylhydroxylamine hydrochloride (1.55 g, 15.86 mmol), and EDCI (3.65 g, 19.03 mmol) in CH2Cl2 (10 mL). The mixture was stirred at room temperature for 72 hours then quenched with saturated aqueous NaHCO3. Water (50 mL) was added followed by additional CH2Cl2. The mixture was stirred for 10 minutes and layers were separated. The CH2Cl2 layer was dried over Na2SO4, then filtered. The solvent was removed under reduced pressure and the residual oil chromatographed (CH2Cl2/EtOAc) to provide the title compound as a solid.

Provenance & Evidence