Imidazole → HCID 131731316, compound

Participants

Reaction Steps

Synthesis of 4-chloro-1H-imidazole (C33). To a solution of 1H-imidazole (22.1 g, 324 mmol) in N,N-dimethylformamide at 0° C. was added drop-wise (over 4 hours) a solution of N-chlorosuccinimide (25 g, 190 mmol) in N,N-dimethylformamide (total solvent, 160 mL). The reaction was stirred at 0° C. for 1 hour, whereupon water (200 mL) was added at 0° C. The mixture was extracted with ethyl acetate (3×50 mL), and the combined organic layers were concentrated in vacuo. Purification was carried out using supercritical fluid chromatography (Column: Princeton Cyano, 5 μm; Eluant: 15:85 methanol/carbon dioxide). The resulting material was purified again, using silica gel chromatography (Mobile phase A: ethyl acetate; Mobile phase B: [20% (2 M ammonia in methanol) in dichloromethane]; Gradient: 0% to 10% B) to afford the title compound as a white solid. Yield: 2.45 g, 23.9 mmol, 12%. GCMS m/z 102, 104 (M+). 1H NMR (400 MHz, CDCl3) δ 7.00 (d, J=1.2 Hz, 1H), 7.57 (br s, 1H), 11.3 (v br s, 1H).

Provenance & Evidence