Phthalimide → 2-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione

HRID 2297297Notes

Reaction equation

HRID 2297297 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4](=[O:7])[CH2:5]Cl.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4](=[O:7])[CH2:5][N:17]1[C:13](=[O:23])[C:14]2[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:16]1=[O:18]

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 10796Cesium carbonateHCID 202502,2',4'-Trichloroacetophenone

Product 1

HCID 7367782-[2-(2,4-dichlorophenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1 mmol of 2,4-dichlorophenacyl chloride in DMF was added drop wise to 2 mmol of phthalimide and 2 mmol of Cs2CO3 in DMF at room temperature for fourteen hours and then the reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The ethyl acetate layer was concentrated and then purified by trituration with diethyl ether.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with water and ethyl acetate
  3. concentrationThe ethyl acetate layer was concentrated
  4. custompurified by trituration with diethyl ether

Sources & evidence

ORD record
ord-3048a1f053c5450981a9cb0f38572df4
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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