4-Chlorophenyl Isocyanate → HCID 67795264, compound

HRID 1034237Notes

Reaction equation

HRID 1034237 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[NH2:11][CH:12]1[C:16](=[O:17])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][CH:13]1[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C@H:12]2[C:16](=[O:17])[N:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:14][C@H:13]2[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 19023543HCID 19023543, compound

Product 1

HCID 67795264HCID 67795264, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chlorophenyl isocyanate (113 mg, 0.734 mmol) in CH2Cl2 (1 ml) was added the aminopyrrolidinone of Example R (178 mg, 0.734 mmol) in CH2Cl2 (1 ml). After stirring for 18 h, the solvent was removed in vacuo and the resulting mixture was chromatographed on silica gel (5% EtOH/CH2Cl2) to give the title compound (210 mg, 72%). 'H NMR (300 MHz, CDCl3) δ7.99 (1H, s), 7.42 (2H, d), 7.24 (2H, t), 6.21 (1H, d), 4.92 (1H, q), 4.21 (1H, m), 4.11 (1H, m), 3.55 (2H, q), 3.32 (2H, m), 1.55 (2H, q), 1.29 (4H, m), 1.21 (2H, t), 0.89 (3H, t).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe resulting mixture was chromatographed on silica gel (5% EtOH/CH2Cl2)

Sources & evidence

ORD record
ord-78f9db4dc5ad458e858ff289da725796
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

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