Sodium Chloride → 1-(3-Chloro-2-hydroxypropyl)-2-nitroimidazole

Participants

Reaction Steps

To 1.15 gram of 2-nitroimidazole in 20 mL of absolute ethanol was added 100 mg of potassium carbonate and 1.0 gram (R)-epichlorohydrin. The reaction mixture was refluxed overnight. The cooled reaction mixture is added to 150 mL of saturated aqueous sodium chloride containing 5% sodium bicarbonate. The reaction mixture was extracted with ethyl acetate (3×10 mL ) and the organic extract was dried over anhydrous sodium sulfate, filtered and concentrated to give 1.87 gram of the R enantiomer of 1-(2-hydroxy-3-chloropropyl)-2-nitroimidazole. A similar reaction procedure starting with (S)-epichlorohydrin gives 1.45 gram of the S enantiomer.

Provenance & Evidence