Hydrochloric Acid → HCID 22316826, compound

HRID 396796Notes

Reaction equation

HRID 396796 reaction equation
F[C:2]1[CH:3]=[C:4]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][CH:18]=3)=[CH:15][C:14]([C:28]([O:30]CC)=[O:29])=[N:13]2)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[OH-].[Na+].O.Cl.[CH2:37]([OH:39])[CH3:38]>>[CH2:37]([O:39][C:6]1[CH:5]=[C:4]([N:12]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[O:24][CH:25]=[CH:26][CH:27]=4)=[CH:19][CH:18]=3)=[CH:15][C:14]([C:28]([OH:30])=[O:29])=[N:13]2)[CH:3]=[CH:2][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10])[CH3:38]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962Water2×HCID 14798Sodium HydroxideHCID 22316794HCID 22316794, compound

Product 1

HCID 22316826HCID 22316826, compoundYield 73%

Procedure

To a stirred solution of ethyl 1-[3-fluoro-4-(methylsulfonyl)phenyl]-5-[4-(2-furyl)phenyl]-1H-pyrazole-3-carboxylate (0.57 g, 1.25 mmol) in ethanol (15 mL) was added 2N-NaOH solution in water (1.6 mL, 3.14 mmol), and the mixture was heated at reflux temperature for 30 minutes. After cooling, 2N-HCl solution (4 mL) and water (30 mL) were added to the mixture. The whole was extracted with ethyl acetate (20 mL×3), the organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting solid was washed with methylene chloride to give the title compound (0.413 g, 73.0%, yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 30 minutes
  3. temperatureAfter cooling
  4. extractionThe whole was extracted with ethyl acetate (20 mL×3)
  5. washthe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. washThe resulting solid was washed with methylene chloride

Sources & evidence

ORD record
ord-2732411f6748466585a720439f6c5aab
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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