Phthalimide → HCID 15167900, compound

HRID 1494853Notes

Reaction equation

HRID 1494853 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[CH2:5]Cl.[K].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12>CN(C=O)C>[C:12]1(=[O:22])[N:16]([CH2:5][C:4]2[CH:3]=[C:2]([CH3:1])[C:9]([CH3:10])=[CH:8][CH:7]=2)[C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 660183,4-Dimethylbenzyl chlorideHCID 5462222Potassium

Product 1

HCID 15167900HCID 15167900, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

92.8 g of 3,4-dimethylbenzyl chloride and 116.7 g of potassium salt of phthalimide were dissolved in 600 ml of DMF and the solution was heated under reflux for 20 hours. After cooling, insoluble materials were removed by filtration and the filtrate was concentrated. The residue was dissolved in chloroform, washed with 0.1 N aqueous sodium hydroxide and then with water, and concentrated. 140 g of 4-phthalimidomethyl-o-xylene was obtained by recrystallization from a chloroform-ether mixed solvent.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 20 hours
  3. temperatureAfter cooling
  4. custominsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in chloroform
  7. washwashed with 0.1 N aqueous sodium hydroxide
  8. concentrationwith water, and concentrated

Sources & evidence

ORD record
ord-930466d2e4204d32977ef96b1bff1dda
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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