Water → 2-(4-Methylpent-3-en-1-yl)-1H-isoindole-1,3(2H)-dione

HRID 324920Notes

Reaction equation

HRID 324920 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][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18].O>CN(C)C=O>[CH3:18][C:17]([CH3:19])=[CH:16][CH2:15][CH2:14][N:5]1[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]2[C:4]1=[O:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 1375215-Bromo-2-methyl-2-penteneHCID 5462222Potassium

Product 1

HCID 132638822-(4-Methylpent-3-en-1-yl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of phthalimide, potassium derivative (11.5 g, 0.062 mol) in dry dimethylformamide (60 mL) was added 1-bromo4-methyl-3-pentene (10.0 g, 0.061 mol) and the suspension was stirred under N2 at 90° C. for 4 h. The reaction mixture was poured into water (300 mL) and the precipitated solid was filtered and washed with water and the solid was dried under vacuum. Yield: 12.8 g (91%). mp 95-97° C. MS: (M+H)+=229.9.

Workup

  1. filtrationthe precipitated solid was filtered
  2. washwashed with water
  3. customthe solid was dried under vacuum

Sources & evidence

ORD record
ord-44070f51606a4e3fbc8be368d791005d
Source dataset
uspto-grants-2001_04
Patent number
US06221334B1

Reaction notes

Loading…