4'-Fluoroacetophenone → 1-[4-(4-Methyl-1H-imidazol-1-yl)phenyl]ethan-1-one

HRID 1886164Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886164
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:11][C:12]1[N:13]=[CH:14][N:15]([C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=2)[CH:16]=1

Komponenten

5

Edukt 3

HCID 98284'-FluoroacetophenoneHCID 11430Potassium CarbonateHCID 178418800HCID 178418800, Verbindung

Produkt 1

HCID 150053821-[4-(4-Methyl-1H-imidazol-1-yl)phenyl]ethan-1-oneAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 4'-fluoroacetophenone (13.8 g, 100 mmol), 4-methylimidazole (8.2 g, 100 ml) and potassium carbonate (20.7 g, 150 mmol) in dry dimethylformamide (190 ml) was heated at 150° C. for 23 hours. Most of the solvent was evaporated at reduced pressure and the residue was partitioned between ethyl acetate and brine. The organic layer was washed (3×) with brine, dried (magnesium sulphate) and evaporated to leave a sticky solid which was purified by flash chromatography (eluting 5% diethylamine in ethylacetate). Recrystallization from ethyl acetate/hexane afforded the title compound (yield 4 g, 20%), m.p. 100° C.

Aufarbeitung

  1. customMost of the solvent was evaporated at reduced pressure
  2. customthe residue was partitioned between ethyl acetate and brine
  3. washThe organic layer was washed (3×) with brine
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. customto leave a sticky solid which
  7. customwas purified by flash chromatography (eluting 5% diethylamine in ethylacetate)
  8. customRecrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9c0706f518464777bfc29d6af3b235f9
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05149814

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