616-47-7

79-22-1

62366-53-4

In a 100 mL three-necked flask protected with argon, 22 mL of acetonitrile and 6.3 mL of methyl chloroformate were added and the mixture was cooled to -20°C. A solution of 3.3 g N-methylimidazole and 6.8 mL triethylamine dissolved in 8 mL of acetonitrile was slowly added dropwise for a controlled time of 30 minutes. After the dropwise addition, the reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, 50 mL of ethyl acetate was added to the reaction solution, the insoluble material was removed by filtration and the solid residue was washed with 50 mL of ethyl acetate. The filtrate and washings were combined and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography with the eluent being a mixed solvent of hexane/ethyl acetate to give 4.2 g of methyl 1-methyl-1H-imidazole-2-carboxylate in 73% yield.