Epichlorohydrin → 2-Chloro-1-(3-chloro-2-hydroxypropyl)-4-nitroimidazole

Sodium 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.

1. temperatureunder reflux for 4 hours
2. customto return to room temperature
3. concentrationconcentrated under reduced pressure
4. additionTo the residue, water (20 ml) was added
5. extractionthe resulting mixture was extracted with methylene chloride (15 ml) twice
6. dry with materialthe extracts were dried over sodium sulfate
7. filtrationfiltrated
8. concentrationThe filtrate was concentrated under reduced pressure
9. customthe residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/1)

ORD record

ord-a9fe4db7069540b48be462482aaf123b

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262212B2