Dimethylformamide → 1H-Isoindole-1,3(2H)-dione, 2-(2-phenyl-2-propenyl)-

HRID 918406Notes

Reaction equation

HRID 918406 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].BrC([CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C.[CH3:24]N(C)C=O>O>[C:18]1([C:17](=[CH2:16])[CH2:24][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24194345Phthalimide potassium saltHCID 54076010HCID 54076010, compound

Product 1

HCID 6218261H-Isoindole-1,3(2H)-dione, 2-(2-phenyl-2-propenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 60 g of potassium pthalimide and 66.4 g of α-bromoethyl styrene (prepared by the method of S. F. Reed, Jr., J. Org. Chem., 30, 3258 (1965)) in 150 ml of dimethylformamide is refluxed for 2 hours, cooled, and diluted with 400 ml of water. The resulting solid is filtered and dried in vacuo to give 83.4 g of N-(2-phenyl-2-propenyl)-pthalimide. A small sample that is recrystallized from acetone-hexane has a melting point of 118°-121°C.

Workup

  1. customprepared by the method of S
  2. temperaturecooled
  3. filtrationThe resulting solid is filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a30906bcf799474a9139900c8ac10fd9
Source dataset
uspto-grants-1976_07
Patent number
US03971773

Reaction notes

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