2-Chloroethyl isocyanate → HCID 90426387, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-(−)-tetrahydro-3-furylamine p-toluenesulfonate salt (0.5 g, 1.928 mmol) in THF (20 mL) was gently agitated with MP-Carbonate Resin (1.825 g, 5.78 mmol, 3.17 mmol/g loading) for 36 h, the resin removed via filtration and the filtrate cooled to 0° C., treated drop-wise with chloroethyl isocyanate (0.224 g, 2.121 mmol), warmed to RT and stirred overnight. The mixture was washed with satd. NH4Cl (1×), satd. NaHCO3 (1×), then brine (1×), dried over MgSO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford (S)-1-(2-chloroethyl)-3-(tetrahydrofuran-3-yl)urea (0.11 g, 30%). 1H NMR (400 MHz, DMSO-d6): δ 6.31 (d, J=6.9 Hz, 1 H), 6.01 (t, J=5.9 Hz, 1 H), 4.11-4.08 (m, 1 H), 3.69-3.67 (m, 3 H), 3.55 (t, J=6.2 Hz, 2 H), 3.36 (dd, J=8.8, 3.8 Hz, 1 H), 3.32-3.26 (m, 2 H), 2.03 (dq, J=12.6, 7.6 Hz, 1 H), 1.59-1.61 (m, 1 H); MS (ESI) m/z: 193.1 (M+H+).

Provenance & Evidence