C(=O)([O-])O.[Na+].[Cl:6][C:7]1[NH:8][CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[N:11]=1.[CH2:15]([CH:17]1[O:19][CH2:18]1)[Cl:16]>C(#N)C>[Cl:6][C:7]1[N:8]([CH2:18][CH:17]([OH:19])[CH2:15][Cl:16])[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[N:11]=1Sodium hydrogencarbonate (1.25 g, 14.91 mmol) was added to a solution of 2-chloro-4-nitro-1H-imidazole (2 g, 13.56 mmol) and epichlorohydrin (1.38 g, 14.91 mmol) in acetonitrile (60 ml), and the resulting mixture was stirred under reflux for 4 hours. The reaction mixture was allowed to return to room temperature, and concentrated under reduced pressure. To the residue, water (20 ml) was added, the resulting mixture was extracted with methylene chloride (15 ml) twice, and the extracts were dried over sodium sulfate, and then filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1) to afford 2-chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole (2.04 g, yield 63%) as a light yellow oil.
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