Acetyl chloride → N-(4-fluorophenyl)acetamide

HRID 1977661Notes

Reaction equation

HRID 1977661 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH3:9][C:8]([NH:17][C:16]1[CH:18]=[CH:19][C:13]([F:12])=[CH:14][CH:15]=1)=[O:10]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 97314-Fluoroaniline

Product 1

HCID 9601N-(4-fluorophenyl)acetamideYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (31 ml) and acetyl chloride (15 ml) were added dropwise to a chloroform (100 ml) solution of 4-fluoroaniline (22.3 g) in this order under ice-cooling. The reaction mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. The thus-obtained solid was washed with water, collected by filtration, and recrystallized from ethanol-water to obtain colorless crystals of 4-fluoroacetanilide (25.5 g; yield, 83%).

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. washThe thus-obtained solid was washed with water
  4. filtrationcollected by filtration
  5. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-a1fda9e6ed42468390d99b5c1bd8bf8d
Source dataset
uspto-grants-2001_05
Patent number
US06235730B1

Reaction notes

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