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

Participants

Reaction Steps

Epichlorohydrin (100 mL) was added to a mixture of 2-nitroimidazole (11.3 g, 0.1 mol) and 1 g of potassium carbonate and the solution refluxed for 15-20 min until all 2-nitroimidazole was dissolved. The hot solution was filtered and the yellow crystal was collected to give compound (5, 17 g, 83%). 1H NMR (DMSO-d6, δppm): 3.61 (m, 2H, Cl—CH2—), 4.06 (m, 1H, HO—CH—), 4.32 (dd, 1H, N—CHa—, J=13.8 Hz, 8.4 Hz), 4.63 (dd, 1H, N—CHb—, J=13.8 Hz, 3.6 Hz), 5.67 (d, 1H, OH, J=5.7 Hz), 7.15 (s, 1H, —CH═), 7.56 (s, 1H, —CH═). 13C NMR (DMSO-d6, δppm):46.81, 52.27, 68.75, 127.40, 128.45, 144.98.

Provenance & Evidence