Imidazole → 1-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone

HRID 1582614Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582614
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:7][C:8]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[OH:17])=[O:9]>CN(C)C=O>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]([OH:17])=[C:10]([C:8](=[O:9])[CH2:7][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:15]=1

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 27568852-Bromo-5'-chloro-2'-hydroxyacetophenone2×

Produkt 1

HCID 129536551-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanoneAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (17.9 g, 0.26 mol) was added to a solution of 2-bromo-1-(5-chloro-2-hydroxyphenyl)-1-ethanone [compound (4-1)] (21.8 g, 87.7 mmol) in N,N-dimethylformamide (50 mL), and the resultant mixture was stirred for 17 hours at room temperature. The reaction mixture was added to ice-water, followed by extraction with ethyl acetate. The organic layer was washed with water, and dried over magnesium sulfate. Subsequently, the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography, followed by drying under reduced pressure, to thereby yield 1-(5-chloro-2-hydroxyphenyl)-2-(1H-1-imidazolyl)-1-ethanone as colorless crystals (17.1 g, yield: 82.4%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customSubsequently, the solvent was removed under reduced pressure
  5. customThe residue was purified through silica gel column chromatography
  6. customby drying under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a2e803ce38484b88960817480b1e54ba
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06737434B2

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