3-(Trifluoromethyl)aniline → Acetamide, N-(3-(trifluoromethyl)phenyl)-

HRID 1470626Notes

Reaction equation

HRID 1470626 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13].C(N(CC)CC)C>CN(C1C=CN=CC=1)C.O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([NH:9][C:12](=[O:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 7918Acetic AnhydrideHCID 8471Triethylamine

Product 1

HCID 9595Acetamide, N-(3-(trifluoromethyl)phenyl)-

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-trifluoromethyl-phenylamine (4 g, 24.8 mmol), acetic anhydride (10.1 g, 99.3 mmol), DMAP (0.9 g, 7.4 mmol) and triethyl amine (2.5 g, 24.8 mmol) was heated to reflux 2 h. After completion of the reaction, the reaction mixture was cooled to room temperature, diluted with water, extracted with ethyl acetate, and the combined organic layers were dried over sodium sulphate and concentrated to dryness. The obtained residue was purified by column chromatography using 30% ethylacetate in hexane to get the title compound as off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux 2 h
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. dry with materialthe combined organic layers were dried over sodium sulphate
  6. concentrationconcentrated to dryness
  7. customThe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-dd60278e7ced4350be5de8c2c7b4ceff
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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