Water → 2'-Benzoyl-2,2,2-trichloro-4'-trifluoromethylacetanilide

HRID 1022413Notes

Reaction equation

HRID 1022413 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(N(CC)CC)C.[Cl:27][C:28]([Cl:33])([Cl:32])[C:29](Cl)=[O:30].O>C(Cl)(Cl)Cl>[C:4]([C:3]1[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=[CH:15][C:2]=1[NH:1][C:29](=[O:30])[C:28]([Cl:33])([Cl:32])[Cl:27])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 13014169(2-Amino-5-(trifluoromethyl)phenyl)(phenyl)methanone

Product 1

HCID 124274592'-Benzoyl-2,2,2-trichloro-4'-trifluoromethylacetanilideYield 91.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 762 mg of 2-amino-5-trifluoromethylbenzophenone in 10 ml of chloroform was added dropwise 349 mg of triethylamine, and then 627 mg of trichloroacetyl chloride was added dropwise under ice cooling. After stirring at the same temperature for 30 minutes, 50 ml of water was added, thereby separating layers. The organic layer was collected and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 1.08 g of 2′-benzoyl-2,2,2-trichloro-4′-trifluoromethylacetanilide. 1H NMR (CDCl3): 7.53-7.58 (2H, m), 7.66-7.75 (3H, m), 7.90-7.95 (2H, m), 8.81 (1H, d, J=8.6 Hz), 12.38 (1H, br. s).

Workup

  1. customThe organic layer was collected
  2. concentrationconcentrated
  3. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-a3d11f9f5fa8455ea8b146d028b47d93
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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