Imidazole → Ethyl 4-(1H-imidazol-1-yl)benzoate

HRID 355738

Reaktionsgleichung

Reaktionsgleichung von HRID 355738
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.F[C:7]1[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Produkt 1

HCID 13423940Ethyl 4-(1H-imidazol-1-yl)benzoateAusbeute 56,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Imidazole (0.816 g, 0.01 mol), ethyl 4-fluorobenzoate (2 g, 0.01 mol) and anhydrous potassium carbonate (1.43 g, 0.011 mol) was dissolved in DMSO (30 ml) and heated to 90° C. for 18 h. The solution was poured into water (50 ml), extracted with ethyl acetate (50 ml), dried (sodium sulphate), filtered and evaporated to dryness under reduced pressure. The white solid was purified by flash column chromatography (silica, diethyl ether) to afford a white solid (1.22 g, 56%).

Aufarbeitung

  1. extractionextracted with ethyl acetate (50 ml)
  2. dry with materialdried (sodium sulphate)
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. customThe white solid was purified by flash column chromatography (silica, diethyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-a3d33c33f5864abeb2dabc05dc915596
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834471

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