2-Chloroethyl isocyanate → HCID 90425773, compound

Participants

Reaction Steps

A 0° C. solution of 3-oxetanamine (0.200 g, 2.74 mmol) in THF (15 mL) was treated drop-wise with 2-chloroethyl isocyanate (0.257 mL, 3.01 mmol), allowed to warm to RT as the cooling bath expired, then concentrated to dryness. The residue was treated with toluene and concentrated to dryness (twice) to afford a white solid. The solid was dissolved in THF (15 mL), cooled to −20° C., under Ar, treated with NaH (60% in mineral oil, 0.274 g, 6.84 mmol), allowed to warm to RT and stirred overnight. The mixture was cooled to 0° C., quenched with satd. NH4Cl, warmed to RT, treated with brine and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated to dryness. The aqueous layer was treated with solid NaCl until saturated, extracted with 1:1 EtOAc/THF (4×), then frozen and lyophilized. The lyophilized solid was stirred with EtOH for 1 h, the liquid decanted and the process repeated. The EtOH extracts were combined with the EtOAc/THF extracts, concentrated to dryness, then treated with 10% MeOH/DCM and the solids removed via filtration. The filtrate was combined with the initial EtOAc extracts and purified via silica gel chromatography (MeOH/DCM) to afford 1-(oxetan-3-yl)imidazolidin-2-one (270 mg, 69%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 6.52 (s, 1 H), 4.86 (m, 1 H), 4.71 (t, J=6.6 Hz, 2 H), 4.62 (t, J=7.2 Hz, 2 H), 3.58 (m, 2 H), 3.29 (m, 2 H); MS (ESI) m/z: 143.1 (M+H+).

Provenance & Evidence