Methyl iodide → Ethyl 1-methyl-2-phenyl-1H-imidazole-4-carboxylate

Participants

Reaction Steps

3.5 g of ethyl 2-phenyl-1H-5-imidazolecarboxylate was dissolved in 30 ml N,N-dimethylformamide. 0.71 g of sodium hydride was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction solution was ice-cooled again and 1.5 ml methyl iodide was added, followed by stirring at room temperature for 30 minutes. Water and aqueous ammonium chloride solution were added to the reaction solution, followed by extracting with ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 0.6 g of ethyl 1-methyl-2-phenyl-1H-4-imidazole carboxylate with hexane:ethyl acetate=8:1 and 2.2 g of ethyl 1-methyl-2-phenyl-1H-5-imidazolecarboxylate with hexane:ethyl acetate=1:1.

Provenance & Evidence