Tert-Butyl hypochlorite → HCID 56966447, compound

Participants

Reaction Steps

A solution of 3-(2-methoxyethyl)-2,2,5,5-tetramethylimidazolidin-4-one (0.70 g, 3.5 mmol) in methanol (10 mL) was cooled in ice water for 10 minutes, before neat tert-butyl hypochlorite (0.59 mL, 5.25 mmol, 1.5 equiv.) was added in one portion. High pressure liquid chromatography-mass spectroscopy analysis after 5 minutes showed all starting amine had been consumed. After 20 minutes, the mixture was concentrated in vacuo to an oil. The oil absorbed was on silica (2.5 g) and was purified by silica gel flash chromatography (0-4% methanol in dichloromethane) afforded the N-chloro-imidazolidin-4-one as a colorless oil (0.78 g, 95%). 1H NMR (400 MHz, CDCl3) δ 3.55 (t, J=5.8 Hz, 2H), 3.44 (t, J=6.4 Hz, 2H), 3.36 (s, 3H), 1.46 (s, 6H), 1.36 (s, 6H); 13C NMR (100 MHz, CDCl3) δ 172.8, 82.0, 70.1, 65.3, 58.8, 40.5, 25.1, 23.5; LRMS (ESI/APCI) m/z 235 [M+H]+.

Provenance & Evidence