p-Fluoronitrobenzene → 3-(1-cyanocyclopropyl)-N-[2-methyl-5-(4-nitrophenoxy)phenyl]benzamide

HRID 2190368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190368
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([C:13]1([C:16]2[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=2)[C:19]([NH:21][C:22]2[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:23]=2[CH3:29])=[O:20])[CH2:15][CH2:14]1)#[N:12].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:11]([C:13]1([C:16]2[CH:17]=[C:18]([CH:30]=[CH:31][CH:32]=2)[C:19]([NH:21][C:22]2[CH:27]=[C:26]([O:28][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=3)[CH:25]=[CH:24][C:23]=2[CH3:29])=[O:20])[CH2:15][CH2:14]1)#[N:12]

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 673125693-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamide

Produkt 1

HCID 673127463-(1-cyanocyclopropyl)-N-[2-methyl-5-(4-nitrophenoxy)phenyl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 1-fluoro-4-nitrobenzene (3.19 g, 22.5 mmol) and 3-(1-cyanocyclopropyl)-N-(5-hydroxy-2-methylphenyl)benzamide (6.00 g, 20.5 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (4.25 g, 30.8 mmol) and the mixture was stirred at 80° C. for 6 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (300 mL), washed with water (200 mL) and saturated brine (200 mL), successively, 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→40/60), and the obtained solution was concentrated under reduced pressure to give the title compound (9.08 g, quantitatively) as a yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionThe obtained residue was diluted with ethyl acetate (300 mL)
  4. washwashed with water (200 mL) and saturated brine (200 mL)
  5. dry with materialsuccessively, and dried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→40/60)
  9. concentrationthe obtained solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-133f0b6acb654862b12eb3faf27df8d8
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324395B2

Notizen zur Reaktion

Wird geladen…