(3-bromoprop-1-en-2-yl)benzene → 1H-Isoindole-1,3(2H)-dione, 2-(2-phenyl-2-propenyl)-

HRID 267906Notes

Reaction equation

HRID 267906 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].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH2:16]>CN(C)C=O.O>[C:17]1([C:15](=[CH2:14])[CH2:16][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:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 6218261H-Isoindole-1,3(2H)-dione, 2-(2-phenyl-2-propenyl)-Yield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 60 g of potassium phthalimide and 66.4 g of α-bromomethyl 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)phthalimide. 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-5996ab80556345358c7b00a663953abe
Source dataset
uspto-grants-1976_03
Patent number
US03945997

Reaction notes

Loading…