Acetyl chloride → N-(2-Acetylphenyl)acetamide

HRID 2307776Notes

Reaction equation

HRID 2307776 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(N(CC)CC)C.[C:18](Cl)(=[O:20])[CH3:19]>ClCCl>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:18](=[O:20])[CH3:19])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 110862'-Aminoacetophenone

Product 1

HCID 21306N-(2-Acetylphenyl)acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2′-aminoacetophenone (5.0 g, 37 mmol) in dichloromethane (150 mL) at room temperature was treated with triethylamine (5.3 mL, 40 mmol) and acetyl chloride (3.2 mL, 45 mmol), stirred for 3 hours, then washed with water. The aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined extracts were concentrated to provide the desired product (6.5 g, 100%).

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. concentrationthe combined extracts were concentrated

Sources & evidence

ORD record
ord-3b9f31ca73a74ec188b416c2c35fc220
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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