Sodium hydride → 1-(2-(Trifluoromethoxy)ethyl)imidazolidin-2-one

Participants

Reaction Steps

A −20° C. solution of 1-(2-chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea (0.436 g, 1.858 mmol) in THF (20 mL) was treated with NaH (60% in mineral oil, 0.082 g, 2.044 mmol), warmed to RT and stirred overnight. The mixture was cooled to −20° C., treated with additional NaH (60% in mineral oil, 0.082 g, 2.044 mmol) warmed to RT, stirred for 6 h, then quenched with satd. NH4Cl. The mixture was extracted with EtOAc which was dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 1-(2-(trifluoromethoxy)ethyl)imidazolidin-2-one (156 mg, 42%). 1H NMR (400 MHz, DMSO-d6): δ 6.41 (s, 1 H), 4.13 (t, J=5.3 Hz, 2 H), 3.35-3.34 (m, 4 H), 3.22-3.20 (m, 2H); MS (ESI) m/z: 199.1 (M+H+).

Provenance & Evidence