Allyl chloride → N-Allylphthalimide

HRID 1774265Notes

Reaction equation

HRID 1774265 reaction equation
[K].[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12.[CH2:13](Cl)[CH:14]=[CH2:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:15]([N:6]1[C:2](=[O:12])[C:3]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:4]2[C:5]1=[O:7])[CH:14]=[CH2:13]

Participants

5

Reactant 2

HCID 7850Allyl chlorideHCID 24194345Phthalimide potassium salt

Product 1

HCID 224401N-AllylphthalimideYield 42%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of phthalimide potassium salt (20 g, 108 mmol) and tetrabutylammonium bromide (1.04 g, 3.24 mmol, 0.03 equiv) in anhydrous DMF (75 mL) was added allyl chloride (8.84 mL, 108 mmol) at room temperature, and the mixture was stirred at room temperature for 22 h, resulting in a light-yellow suspension. The reaction was quenched by adding cold H2O (150 mL), and the mixture was stirred for 10 min (an ice bath was applied during this time to aid the precipitation). The resulting white suspension was filtered off, washed with H2O (3×50 mL), and air-dried to give N-allylphthalimide (8.5 g, 42% yield) as white solid.

Workup

  1. customresulting in a light-yellow suspension
  2. customThe reaction was quenched
  3. additionby adding cold H2O (150 mL)
  4. stirringthe mixture was stirred for 10 min (an ice bath
  5. customthe precipitation)
  6. filtrationThe resulting white suspension was filtered off
  7. washwashed with H2O (3×50 mL)
  8. customair-dried

Sources & evidence

ORD record
ord-ce57dcbd1b6a496991e6aee9b0dd6deb
Source dataset
uspto-grants-2016_02
Patent number
US09260382B2

Reaction notes

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