Pyridine → N-[4-(trifluoromethyl)phenyl]acetamide

HRID 906328Notes

Reaction equation

HRID 906328 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[CH3:19][C:18]([NH:7][C:6]1[CH:8]=[CH:9][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:4][CH:5]=1)=[O:20]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 99644-(Trifluoromethyl)aniline

Product 1

HCID 67685N-[4-(trifluoromethyl)phenyl]acetamideYield 99.5%

Procedure

4-Trifluoromethylaniline (3.00 g, 18.6 mmol) was dissolved in pyridine (1.62 g, 20.5 mmol), the solution was added with acetic anhydride (2.38 g, 23.3 mmol) with stirring on an ice bath, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and then azeotroped with toluene, and the resulting residue was suspended in hexane, and taken by filtration. The residue was washed with hexane, and then dried under reduced pressure to obtain 4-trifluoromethylacetanilide (3.76 g, 99%) as colorless solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customazeotroped with toluene
  4. filtrationtaken by filtration
  5. washThe residue was washed with hexane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-89618660c15e49d3b278cd74b960d787
Source dataset
uspto-grants-2011_09
Patent number
US08012989B2

Reaction notes

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