Water → HCID 23130715, compound

HRID 2080033Notes

Reaction equation

HRID 2080033 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH2:13]([O:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)(=O)C.O>CN(C)C=O>[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([CH2:25][N:5]2[C:1](=[O:11])[C:2]3[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4]2=[O:6])=[CH:27][CH:28]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 700424-Benzyloxybenzyl chlorideHCID 24194345Phthalimide potassium salt

Product 1

HCID 23130715HCID 23130715, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium phthalimide (20 g, 0.108 mol) was added to a solution obtained by dissolving 4-benzyloxybenzyl chloride (25 g, 0.107 mol) in N,N-dimethylformamide (75 mL), and the solution was stirred for 3 hours under reflux. The reaction solution was allowed to room temperature, then, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, and 2-(4-benzyloxybenzyl)-isoindol-1,3-dione (37 g, quantitatively) was obtained as a pale brown solid.

Workup

  1. customobtained
  2. temperatureunder reflux
  3. customwas allowed to room temperature
  4. customfor partitioning
  5. washthe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3ab4a020d435476a932b54df87ce7fea
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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