Tert-Butyl hypochlorite → 3-Chloro-4-(hydroxymethyl)-1,4-dimethylimidazolidin-2-one

Participants

Reaction Steps

A solution of 4-(hydroxymethyl)-1,4-dimethylimidazolidin-2-one (250 mg, 1.72 mmol) in methanol (2.5 ml) was cooled to 0° C. tert-Butylhypochlorite (236 ul, 2.1 mmol) was added. The resulting solution was stirred for 30 minutes, then concentrated under reduced pressure to a crude residue. The crude material was purified by column chromatography (1 to 12% methanol in dichloromethane) to give the desired product as a white solid (168 mg, 0.941 mmol, 54%). 1H NMR (400 MHz, D2O) δ 1.16 (s, 3H), 2.74 (s, 3H), 3.25-3.27 (d, J=9.2 Hz, 1H), 3.38-3.41 (d, J=12.6 Hz, 1H), 3.47-3.49 (d, J=9.2 Hz, 2H), 3.64-3.67 (d, J=12.6 Hz, 1H). 13C NMR (100 MHz, D2O) δ 18.1, 30.8, 53.2, 62.8, 64.5, 161.6. LRMS (ESI/APCI) m/z 179 [M+H]+.

Provenance & Evidence