2-Chlorobenzyl chloride → N-acetyl-N-(2-chlorobenzyl)-2-phenoxyaniline

HRID 2271195Notes

Reaction equation

HRID 2271195 reaction equation
[H-].[Na+].[C:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:5])[CH3:4].[Cl:20][C:21]1[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=1[CH2:23]Cl>CN(C)C=O>[C:3]([N:6]([CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=1[Cl:20])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 119062-Chlorobenzyl chlorideHCID 24758Sodium hydrideHCID 8970802-Phenoxyacetanilide

Product 1

HCID 18407206N-acetyl-N-(2-chlorobenzyl)-2-phenoxyanilineYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 400 mg of sodium hydride (60% in oil) in 30 ml of dimethylformamide was added 2.00 g of N-acetyl-2-phenoxyaniline at room temperature, followed by stirring at room temperature for 30 minutes. To the solution was added dropwise 1.64 g of 2-chlorobenzyl chloride at room temperature with stirring, followed by stirring for 30 minutes. After addition of ice-water, the reaction mixture was extracted with ether. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:4) to give 2.92 g of N-acetyl-N-(2-chlorobenzyl)-2-phenoxyaniline as an oil.

Workup

  1. stirringwith stirring
  2. stirringby stirring for 30 minutes
  3. extractionthe reaction mixture was extracted with ether
  4. washThe extract was washed with 0.5 N hydrochloric acid
  5. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  6. customAfter removal of the drying agent
  7. filtrationby filtration
  8. concentrationthe solvent was concentrated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate-hexane=1:4)

Sources & evidence

ORD record
ord-157b8ec5bb6f4d62828b88481518bae7
Source dataset
uspto-grants-2001_12
Patent number
US06333358B1

Reaction notes

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