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

HRID 1022405Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1022405
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 124274592'-Benzoyl-2,2,2-trichloro-4'-trifluoromethylacetanilideAusbeute 91,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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 the solution. The organic layer was collected and then 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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3bd280411555419d825f5a63dddf9eee
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722580B2

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