1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 23081493, compound

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.

1. washThe reaction mixture was washed with 3N hydrochloric acid (20 ml)
2. dry with materiala saturated saline solution (20 ml) in this order, dried over sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated under reduced pressure
5. customthe residue was purified by silica gel column chromatography (methylene chloride/ethyl acetate=20/1)

ORD record

ord-d12a79b60ff44a19afddc739a2eb742a

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2