Imidazole → 3-Chloro-4-(1H-imidazol-1-YL)benzaldehyde

HRID 1446457

Reaktionsgleichung

Reaktionsgleichung von HRID 1446457
CN(C=O)C.[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1F)[CH:10]=[O:11].C(=O)([O-])[O-].[K+].[K+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>C(OCC)(=O)C.O>[Cl:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)[CH:10]=[O:11]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 5938663-Chloro-4-fluorobenzaldehyde

Produkt 1

HCID 236294243-Chloro-4-(1H-imidazol-1-YL)benzaldehydeAusbeute 84,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a DMF (20 mL) solution of 3-chloro-4-fluorobenzaldehyde (500 mg), potassium carbonate (1.20 g) and imidazole (275 mg) were added one by one, and the reaction solution was agitated at 80° C. overnight. Water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (elution solvent:ethyl acetate→ethyl acetate:methanol=10:1), and 548 mg of the title compound was obtained. The physical properties of the compound are as follows.

Aufarbeitung

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel chromatography (elution solvent:ethyl acetate→ethyl acetate:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-f817aeb530774094aa5c2d6927a6f704
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667041B2

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