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

Participants

Reaction Steps

A solution of 4-(chloromethyl)-1,4-dimethylimidazolidin-2-one (204 mg, 1.25 mmol) in MeOH (2.5 ml) was cooled to 0° C. tert-Butylhypochlorite (177 ul, 1.57 mmol) was added. The resulting solution was stirred for 60 min, during which time a white precipitate formed. The reaction mixture was concentrated under reduced pressure to half its initial volume and the solid was collected on a glass fritted filter and washed with water to give 168 mg of desired product (69% yield). 1H NMR (400 MHz, CDCl3) δ1.48 (s, 3H), 2.90 (s, 3H), 3.21-3.23 (d, J=8.8 Hz, 1H), 3.52-3.54 (d, J=8.9 Hz, 1H), 3.59-3.67 (q, J=11.1 Hz, 2H). 13C NMR (100 MHz, CDCl3) δ 19.9, 31.7, 47.6, 54.5, 63.1, 158.7. LRMS (ESI/APCI): 197 [M+H]+.

Provenance & Evidence