Water → 3-(1-cyano-1-methylethyl)-N-{3-[(5-nitropyridin-2-yl)oxy]-4-(trifluoromethyl)phenyl}benzamide

HRID 1800499

Reaktionsgleichung

Reaktionsgleichung von HRID 1800499
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[C:24]([OH:32])[CH:23]=1)=[O:20])([CH3:15])[CH3:14])#[N:12].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:11]([C:13]([C:16]1[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=1)[C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:31])[F:30])=[C:24]([O:32][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:23]=1)=[O:20])([CH3:15])[CH3:14])#[N:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 684185013-(1-cyano-1-methylethyl)-N-[3-hydroxy-4-(trifluoromethyl)phenyl]benzamide

Produkt 1

HCID 684185283-(1-cyano-1-methylethyl)-N-{3-[(5-nitropyridin-2-yl)oxy]-4-(trifluoromethyl)phenyl}benzamideAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 2-chloro-5-nitropyridine (2.00 g, 5.74 mmol) and 3-(1-cyano-1-methylethyl)-N-[3-hydroxy-4-(trifluoromethyl)phenyl]benzamide (955 mg, 6.02 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (1.18 g, 8.61 mmol), and the mixture was stirred at 80° C. for 20 hr. After the reaction mixture was cooled to room temperature, water (150 mL) was added, and the mixture was twice extracted with ethyl acetate/hexane (75 mL/75 mL). The combined organic layer was washed with saturated brine (150 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70). The obtained solution was concentrated under reduced pressure to give the title compound (1.79 g, 66%) as a yellow amorphous substance.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. extractionthe mixture was twice extracted with ethyl acetate/hexane (75 mL/75 mL)
  3. washThe combined organic layer was washed with saturated brine (150 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→30/70)
  8. concentrationThe obtained solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7ccec59d610d43e5ac12086bd27c1dfc
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08344135B2

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