4-Chlorophenyl Isocyanate → HCID 67795264, compound

HRID 1590259Notes

Reaction equation

HRID 1590259 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 (1ml). 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-34b12ac30c704be0806b52488738ae03
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

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