Synthesis
To a tetrahydrofuran (THF) solution of 1H-imidazole (5 g, 73.5 mmol) was added sodium hydride (1.8 g, 45 mmol) in batches and stirred at room temperature for 30 minutes. Subsequently, bromoacetonitrile (8.8 g, 73.9 mmol) was slowly added dropwise and stirring was continued for 2 hours at room temperature. Upon completion of the reaction, the reaction was quenched by the addition of water (50 mL) and saturated ammonium chloride solution (50 mL). The reaction mixture was extracted with ethyl acetate (100 mL x 3) and the organic layers were combined. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate=10:1) to give 2-(1H-imidazol-1-yl)acetonitrile (4.6 g, 59% yield) as a yellow oil.LRMS m/z: 108 [M+H]+.
References
[1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 9, p. 3185 - 3198
[2] European Journal of Organic Chemistry, 2018, vol. 2018, # 18, p. 2110 - 2116
[3] New Journal of Chemistry, 2002, vol. 26, # 7, p. 926 - 932
[4] Patent: US2015/65522, 2015, A1. Location in patent: Paragraph 0469; 0470; 0471
[5] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 2009 - 2016
