Acetic Acid → 4-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzoic acid

HRID 1441743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441743
[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13]C(C#N)=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH:4]=[CH:5][N:6]=1.Cl.[C:20]([OH:23])(=[O:22])[CH3:21]>>[CH3:1][C:2]1[N:3]([C:7]2[CH:14]=[CH:13][C:21]([C:20]([OH:23])=[O:22])=[CH:9][C:8]=2[C:15]([F:18])([F:16])[F:17])[CH:4]=[CH:5][N:6]=1

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 686779374-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile

Produkt 1

HCID 686779654-(2-Methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzoic acid

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 4-(2-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile (1.01 g, 4 mmol), 6 mL of acetic acid and 3 mL of 12M hydrochloric acid (37%) is shaken for 16 hours at 95° C. After cooling, the reaction mixture is evaporated to dryness under reduced pressure. The resulting residue is evaporated twice with toluene, dissolved in water and the pH is adjusted to ˜5-6 by dropwise addition of 1M sodium hydroxide solution. The aqueous phase is extracted twice with n-butanol and the organic phase evaporated to yield the title compound as a beige solid.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe reaction mixture is evaporated to dryness under reduced pressure
  3. customThe resulting residue is evaporated twice with toluene
  4. dissolutiondissolved in water
  5. additionthe pH is adjusted to ˜5-6 by dropwise addition of 1M sodium hydroxide solution
  6. extractionThe aqueous phase is extracted twice with n-butanol
  7. customthe organic phase evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f00b2ccadb0540a6bcd110800afd9bef
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655669B2

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