1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Chloro-4-nitro-1-(oxiran-2-ylmethyl)imidazole
Reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH:11]([OH:14])[CH2:12]Cl)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[Cl:1][C:2]1[N:3]([CH2:10][CH:11]2[CH2:12][O:14]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1Participants
4
Procedure
2-Chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole prepared in Example 1 (2.04 g, 8.5 mmol) was dissolved in methylene chloride (20 ml), and 1,8-diazabicyclo[5.4.0]-7-undecene (DBU) (2.04 ml, 13.67 mmol) was added to the solution. The resulting mixture was stirred at room temperature overnight. The reaction mixture was washed with 3N hydrochloric acid (20 ml) and a saturated saline solution (20 ml) in this order, dried over sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1) to afford 2-chloro-4-nitro-1-(oxiran-2-ylmethyl)imidazole (190 mg, yield 11%) as a colorless oil.