Water → N-(3-chloro-2-methylbenzyl)phthalimide

HRID 2390033Notes

Reaction equation

HRID 2390033 reaction equation
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5]Cl.C(=O)([O-])[O-].[K+].[K+].[K].[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.O>C(#N)C>[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][N:22]1[C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]2[C:18]1=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 145997631-Chloro-3-(chloromethyl)-2-methylbenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 59323393N-(3-chloro-2-methylbenzyl)phthalimideYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

700 mg of 3-chloro-2-methylbenzyl chloride was dissolved in 10 mL of acetonitrile, and 829 mg of potassium carbonate and 889 mg of phthalimide potassium were added thereto at room temperature, followed by warming to 80° C., and then continuously reacting overnight. After completion of the reaction, the reaction liquid was left to be cooled, and water was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1.15 g (yield 100%) of a title compound as a white crystal.

Workup

  1. customat room temperature
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. waitwas left
  5. temperatureto be cooled
  6. extractionfollowed by extraction with chloroform
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e417a5467ef45939b2fd62e931f0708
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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