Acetyl chloride → 2-Phenoxyacetanilide

HRID 1016568

Reaction equation

HRID 1016568 reaction equation
[O:1]([C:8]1[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=1[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>C(Cl)Cl>[C:22]([NH:10][C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 75899Benzenamine, 2-phenoxy-

Product 1

HCID 8970802-Phenoxyacetanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 28.5 g of 2-phenoxyaniline and 25.8 ml of triethylamine in 250 ml of methylene chloride was added dropwise 11.5 ml of acetyl chloride under ice-cooling. After stirring at room temperature for 1.5 hours, the reaction mixture was concentrated under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. 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 33.7 g of N-acetyl-2-phenoxyaniline.

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with 0.5 N hydrochloric acid
  6. dry with materiala saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby filtration
  9. concentrationthe solvent was concentrated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

Sources & evidence

ORD record
ord-069f637431ce4028a7981f4478c820ae
Source dataset
uspto-grants-2002_11
Patent number
US06476056B2

Linked notes

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