Hydrochloric Acid → HCID 22288394, compound

HRID 1181260Notes

Reaction equation

HRID 1181260 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C:19]([C:20]([F:23])([F:22])[F:21])=[C:18]([C:24]([O-:26])=[O:25])[CH:17]=[N:16]3)=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]3[C:19]([C:20]([F:23])([F:21])[F:22])=[C:18]([C:24]([OH:26])=[O:25])[CH:17]=[N:16]3)=[CH:13][CH:14]=2)=[O:7])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86757789HCID 86757789, compound

Product 1

HCID 22288394HCID 22288394, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[4-(4-chlorobenzoylamino)phenyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylate (150 mg), 1 N sodium hydroxide aqueous solution (1 ml) and ethanol (2 ml) was stirred at 45° C. for 4 hours. After spontaneous cooling, 1 N hydrochloric acid aqueous solution (2 ml) was added to the reaction solution, the thus formed product was extracted with ethyl acetate and then the extract was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was recrystallized from ethanol to give 1-[4-(4-chlorobenzoylamino)phenyl]-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid (91 mg) as colorless powder crystals.

Workup

  1. extractionthe thus formed product was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under a reduced pressure
  5. customThe resulting residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-b529a8a0e48f4154968da32ed19f64e2
Source dataset
uspto-grants-2007_10
Patent number
US07285554B2

Reaction notes

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