Water → N-[2-(2,4-dichloro-phenyl)-1-methylethyl]-2-trifluoromethylbenzamide

HRID 389173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389173
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([NH2:12])[CH3:11].C(N(CC)CC)C.[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([NH:12][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=1[C:21]([F:20])([F:31])[F:32])[CH3:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 30411751-(2,4-Dichlorophenyl)propan-2-amine

Produkt 1

HCID 67223276N-[2-(2,4-dichloro-phenyl)-1-methylethyl]-2-trifluoromethylbenzamideAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of crude [2-(2,4-dichlorophenyl)-1-methylethyl]amine (about 0.8 g, 3.9 mmol) and triethylamine (0.6 g, 5.9 mmol) in tetrahydrofuran (20 ml) was slowly added dropwise 2-trifluoromethylbenzoyl chloride (0.8 g, 3.8 mmol) at room temperature. After stirring at room temperature for 0.5 hr, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with 0.5N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography and recrystallized from a mixed solvent of acetone/n-hexane to give a desired compound (white solid, yield; 0.4 g, 27%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 0.5N hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography
  6. customrecrystallized from a mixed solvent of acetone/n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ed43c68206b34ce2885e2c589be96686
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378114B2

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