Sodium Hydroxide → HCID 69251381, compound

HRID 746778Notes

Reaction equation

HRID 746778 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[C:10]=1[NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[O:5])C.[OH-].[Na+]>C(O)C>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([N:9]2[C:10]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69253368HCID 69253368, compound

Product 1

HCID 69251381HCID 69251381, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 1-(4-Bromo-phenyl)5-(propane-2-sulfonylamino)-1H-pyrazole-4-carboxylic acid ethyl ester (2.549 g, 6.12 mmol) in ethanol (10 mL)(denatured with methanol) and then add an aqueous solution of sodium hydroxide (12.5 mL, 2.0M). Immerse the resulting mixture into a pre-heated oil bath (65° C.) and stir overnight. Upon completion, concentrate to remove ethanol/methanol, wash the resulting aqueous mixture with dichloromethane, and concentrate to remove any trace of dichloromethane. Cool the aqueous mixture to 0° C., add 1.0 HCl until pH 4 is achieved (extensive precipitation of acid may be observed), and stir for 15 min. Filter the mixture under reduced pressure. Allow the reduced pressure to cool the filtrate, and filter a second crop of product. Combine the two crops to yield 1-(4-Bromo-phenyl)-5-(propane-2-sulfonylamino)-1H-pyrazole-4-carboxylic acid (2.031 g, 85%).

Workup

  1. custom(65° C.)
  2. concentrationUpon completion, concentrate
  3. customto remove ethanol/methanol
  4. washwash the resulting aqueous mixture with dichloromethane
  5. concentrationconcentrate
  6. customto remove any trace of dichloromethane
  7. additionadd 1.0 HCl until pH 4
  8. custom(extensive precipitation of acid may be observed)
  9. stirringstir for 15 min
  10. filtrationFilter the mixture under reduced pressure
  11. temperatureto cool the filtrate
  12. filtrationfilter a second crop of product

Sources & evidence

ORD record
ord-a1765c109b744a6d8721173c411841be
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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