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

HRID 12440

반응식

HRID 12440 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 24841Hydrogen iodide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4325811208714cde96d7855dd97c1686
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728016B2

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