Acetic Acid → 4-(4-methyl-1H-imidazole-1-yl)-3-(trifluoromethyl)benzoic acid

HRID 1441744Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1441744
[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:14]=[CH:13]C(C#N)=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH:6]=1.Cl.[C:20]([OH:23])(=[O:22])[CH3:21]>>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([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:6]=1

Komponenten

4

Edukt 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 686771234-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile

Produkt 1

HCID 686786644-(4-methyl-1H-imidazole-1-yl)-3-(trifluoromethyl)benzoic acid

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzonitrile (1.01 g, 4 mmol), 6 mL of acetic acid and 3 mL of 12 M 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 ethyl acetate. The organic phase is dried (Na2SO4) and evaporated to yield the title compound as a pale yellow 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 ethyl acetate
  7. dry with materialThe organic phase is dried (Na2SO4)
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-76403a98352d43aa901a121e4f79fe8b
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07655669B2

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