Acetic Acid → 1-(2,4-Dihydroxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

HRID 12440

Reaktionsgleichung

Reaktionsgleichung von HRID 12440
Cl[C:2]1[C:3]([O:25]C)=[CH:4][C:5]([O:23]C)=[C:6]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[C:11]([C:20]([OH:22])=[O:21])[N:10]=[N:9]2)[CH:7]=1.C(O)(=O)C.C(OC(=O)C)(=O)C.O>I>[OH:23][C:5]1[CH:4]=[C:3]([OH:25])[CH:2]=[CH:7][C:6]=1[N:8]1[C:12]([C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)=[C:11]([C:20]([OH:22])=[O:21])[N:10]=[N:9]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 587310181-(5-Chloro-2,4-dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

Produkt 1

HCID 114838711-(2,4-Dihydroxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24841Hydrogen iodideLösungsmittel

Versuchsvorschrift

1-(5-Chloro-2,4-dimethoxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (0.29 g, 0.77 mmol) was refluxed in a mixture of hydroiodic acid (5 mL), acetic acid (1 mL) and acetic anhydride (0.5 mL) for 16 hours. When cooled, water (20 mL) was added and the aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were washed with saturated sodium thiosulphate solution (2×15 mL) and brine (20 mL), dried with NaSO4 and filtered. After evaporation of the solvent, light brown solids were obtained (0.15 g, 62%). The compound was used in the next synthetic step without further purification.

Aufarbeitung

  1. temperatureWhen cooled
  2. extractionthe aqueous layer was extracted with EtOAc (2×15 mL)
  3. washThe combined organic layers were washed with saturated sodium thiosulphate solution (2×15 mL) and brine (20 mL)
  4. dry with materialdried with NaSO4
  5. filtrationfiltered
  6. customAfter evaporation of the solvent
  7. customlight brown solids were obtained (0.15 g, 62%)
  8. customThe compound was used in the next synthetic step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-4325811208714cde96d7855dd97c1686
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728016B2

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