Hydrochloric Acid → HCID 22316826, compound

HRID 497235Notes

Reaction equation

HRID 497235 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-9266039725054510a098a1dbe80d4a2e
Source dataset
uspto-grants-2005_09
Patent number
US06949536B2

Reaction notes

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