3,4-Dichlorophenyl isocyanate → Ethyl cis-4-[[[(3,4-dichlorophenyl)amino]carbonyl]amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

HRID 1034232Notes

Reaction equation

HRID 1034232 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:12][CH:13]1[C:17](=[O:18])[N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH:14]1[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C@H:13]2[C:17](=[O:18])[N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][C@H:14]2[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 76073,4-Dichlorophenyl isocyanateHCID 19023548Ethyl 4-amino-5-oxo-1-phenyl-3-pyrrolidinecarboxylate

Product 1

HCID 67794020Ethyl cis-4-[[[(3,4-dichlorophenyl)amino]carbonyl]amino]-5-oxo-1-phenyl-3-pyrrolidinecarboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3,4-dichlorophenylisocyanate in CH2Cl2 (3 ml) was added a solution of aminopyrrolidinone of Example S (350 mg, 1.41 mmol) in CH2Cl2 (3 ml) and the resulting solution was stirred for 18 h at room temperature. Concentration in vacuo gave a solid which was triturated with CH2Cl2 and filtered to give the title compound (420 mg, 68%) as a solid. MS M+1 calcd for C20H19N3O4Cl2 437, found 437. DSC=249.1°-251.7° C. at 112.7 J/g.

Workup

  1. concentrationConcentration in vacuo
  2. customgave a solid which
  3. customwas triturated with CH2Cl2
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ec4018bda5254b60a6fea5848f9438bc
Source dataset
uspto-grants-1994_05
Patent number
US05314886

Reaction notes

Loading…