Hydrochloric Acid → 4-(1-Imidazolyl)benzoic Acid

HRID 247592

Reaktionsgleichung

Reaktionsgleichung von HRID 247592
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.[OH-].[Na+].O>[N:12]1([C:2]2[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:16]=[CH:15][N:14]=[CH:13]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 11430Potassium CarbonateHCID 67878Methyl 4-fluorobenzoate

Produkt 1

HCID 7365294-(1-Imidazolyl)benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

Combine methyl 4-fluorobenzoate (1.52 g, 10 mmol), 1H-imidazole (0.82g, 12 mmol) and potassium carbonate (1.40 g, 10 mmol) in dimethylsulfoxide (7 mL) and heat the mixture with stirring at 120°-130° C. for 5 hours, cool, add water and acid, extract with ether. Adjust the pH of the aqueous layer to 8 with sodium carbonate, extract with ether, dry the extract with sodium sulfate and evaporate. 4-(1H-Imidazol -1-yl)benzoic acid is prepared by refluxing this methyl ester (0.61 g, 3 mmol) in 5 mL of 10% aqueous sodium hydroxide for five minutes; cool, neutralize to pH 6-7 with hydrochloric acid, filter and dry the precipitated acid.

Aufarbeitung

  1. temperaturecool
  2. extractionextract with ether
  3. extractionextract with ether
  4. customdry the
  5. extractionextract with sodium sulfate
  6. customevaporate
  7. filtrationfilter
  8. customdry the precipitated acid

Quellen und Nachweise

ORD-Eintrag
ord-1da2c005a2d8428ba59bce9b6c23a38f
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04709043

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