2-(Trifluoromethyl)aniline → Acetamide, N-(2-(trifluoromethyl)phenyl)- (9CI)

HRID 408120Notes

Reaction equation

HRID 408120 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[C:12](OC(=O)C)(=[O:14])[CH3:13]>O>[C:12]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[CH:9][C:3]=1[C:2]([F:10])([F:11])[F:1])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 69222-(Trifluoromethyl)anilineHCID 7918Acetic Anhydride

Product 1

HCID 67655Acetamide, N-(2-(trifluoromethyl)phenyl)- (9CI)Yield 92.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Commercial o-trifluoromethylaniline (13.5 g, 83.9 mmol) was dissolved in acetic anhydride (55 mL, 580.0 mmol) and stirred at room temperature for 1 h. Then the reaction mixture was poured into H2O, the whole was extracted with ethyl acetate (2×300 mL). The combined organic extracts were washed with 5% aqueous NaHCO3, brine, dried (K2CO3), filtered and concentrated to provide the title compound as a white solid (15.7 g, 92%).

Workup

  1. extractionthe whole was extracted with ethyl acetate (2×300 mL)
  2. washThe combined organic extracts were washed with 5% aqueous NaHCO3, brine
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-56609508cb8f403aa672c4a173b50d25
Source dataset
uspto-grants-2014_06
Patent number
US08759336B2

Reaction notes

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