Sodium Chloride → 1-Cyclohexyl-2-imidazolidinone

Participants

Reaction Steps

A solution of cyclohexylamine (1.00 g, 10.08 mmol) and 2-chloro ethylisocyanate (1.064 g, 10.08 mmol) in THF (30 mL) was stirred at RT for 4 h, treated with sodium hydride (60% in mineral oil, 0.403 g, 10.08 mmol) and stirred at RT for 16 h. The mixture was poured into satd. NH4Cl, treated with solid NaCl until saturated, extracted with THF (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness. The material was suspended in 30% EtOAc/Hex, stirred and the resulting solid collected via filtration to afford 1-cyclohexylimidazolidin-2-one (650 mg, 38%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.14 (s, 1 H), 3.46-3.37 (m, 1 H), 3.27-3.21 (m, 2 H), 3.19-3.13 (m, 2 H), 1.75-1.68 (m, 2 H), 1.60-1.50 (m, 3 H), 1.37-1.18 (m, 4 H), 1.09-0.98 (m, 1 H).

Provenance & Evidence