2-Chloroethyl isocyanate → HCID 90426387, compound
Reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:12]1[CH2:16][CH2:15][C@H:14]([NH2:17])[CH2:13]1.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O.[Cl:36][CH2:37][CH2:38][N:39]=[C:40]=[O:41]>C1COCC1>[Cl:36][CH2:37][CH2:38][NH:39][C:40]([NH:17][C@H:14]1[CH2:15][CH2:16][O:12][CH2:13]1)=[O:41]Participants
Conditions
- Temperature
- 0 °C
Procedure
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+).
Workup
- customthe resin removed via filtration
- temperaturewarmed to RT
- washThe mixture was washed with satd
- dry with materialNaHCO3 (1×), then brine (1×), dried over MgSO4
- concentrationconcentrated to dryness
- custompurified via silica gel chromatography (MeOH/DCM)
Sources & evidence
- ORD record
- ord-670d3fb52e2844f79bb765ad5c09b074
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133183B2
Reaction notes
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