Acetyl chloride → N-(2-Acetylphenyl)acetamide

HRID 1470645Notes

Reaction equation

HRID 1470645 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11](Cl)(=[O:13])[CH3:12]>ClC(Cl)C>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:11](=[O:13])[CH3:12])(=[O:10])[CH3:9]

Participants

4

Procedure

To an ice cold slurry of the 1-(2-amino-phenyl)-ethanone (2 g, 14.79 mmol) in dichloroethane (10 mL), acetyl chloride (1.22 g, 16.2 mmol) was added slowly. The reaction mixture was warmed to room temperature and stirred for 2 h. After completion of the reaction, the reaction mixture was quenched with water (10 mL) and extracted with dichloromethane (2×25 mL). The combined organic layers were washed with an aq. solution of 5% NaHCO3 followed by water and brine, then dried over anhydrous sodium sulphate and concentrated to dryness. The obtained residue was purified by column chromatography using 2% ethyl acetate in hexane to obtain the title compound as off-white solid which directly used for the next reaction.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction mixture was quenched with water (10 mL)
  3. extractionextracted with dichloromethane (2×25 mL)
  4. washThe combined organic layers were washed with an aq. solution of 5% NaHCO3
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated to dryness
  7. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-09431f2e228748049a20b97d96a03820
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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