Ethanol → 1-(2,4-Dihydroxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

HRID 12441Notes

Reaction equation

HRID 12441 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:12]([C:21]([OH:23])=[O:22])[N:11]=[N:10]1.[CH3:24][CH2:25]O>OS(O)(=O)=O>[CH2:24]([O:22][C:21]([C:12]1[N:11]=[N:10][N:9]([C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[OH:1])[C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)=[O:23])[CH3:25]

Participants

4

Reactant 2

HCID 702EthanolHCID 114838711-(2,4-Dihydroxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid

Product 1

HCID 587310161-(2,4-Dihydroxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

1-(2,4-Dihydroxy-phenyl)-5-(4-fluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (0.15 g, 0.48 mmol) was refluxed in EtOH (20 mL) in the presence of 5 drops of concentrated H2SO4 for 3 hours. After evaporation of the solvent, EtOAc (20 mL) was added. The organic layer was then washed with sat. NaHCO3 (2×10 mL) and brine (20 mL), dried with NaSO4 and filtered. After evaporation of the solvent, light brown semi-solids (93 mg, 57%) were obtained and purified by prep. TLC (Rf=0.73, EtOAc).

Workup

  1. customAfter evaporation of the solvent, EtOAc (20 mL)
  2. additionwas added
  3. washThe organic layer was then washed with sat. NaHCO3 (2×10 mL) and brine (20 mL)
  4. dry with materialdried with NaSO4
  5. filtrationfiltered
  6. customAfter evaporation of the solvent
  7. customlight brown semi-solids (93 mg, 57%) were obtained
  8. custompurified by prep

Sources & evidence

ORD record
ord-71fa31f77a6743d998658e65f9b69f56
Source dataset
uspto-grants-2010_06
Patent number
US07728016B2

Reaction notes

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