Sodium Hydroxide → HCID 66958955, compound

HRID 1360486Notes

Reaction equation

HRID 1360486 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][CH2:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:14])=[O:13])=[CH:8][C:7]([C:18]([O:20]CC)=[O:19])=[N:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+]>C(O)C>[CH2:1]([N:5]1[C:9]([CH2:10][CH2:11][S:12]([CH2:15][CH2:16][CH3:17])(=[O:13])=[O:14])=[CH:8][C:7]([C:18]([OH:20])=[O:19])=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66958861HCID 66958861, compound

Product 1

HCID 66958955HCID 66958955, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 1-butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carboxylate (5.00 g, 15.1 mmol) in ethanol (76 mL) at ambient temperature was added 6 M aqueous sodium hydroxide (5.0 mL, 30 mmol). The solution was stirred for 2 hours, then the volatiles were removed under reduced pressure and the resulting oil was dissolved in water (100 mL). The aqueous solution was washed with dichloromethane (50 mL) and then the pH was adjusted with 1 M hydrochloric acid to pH 4. A precipitate formed and the mixture was stirred for 1 hour. The solid was isolated by filtration, washed with water, and dried to provide 4.6 g of 1-butyl-5-[2-(propylsulfonyl)ethyl]-1H-pyrazole-3-carboxylic acid as a white powder.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionthe resulting oil was dissolved in water (100 mL)
  3. washThe aqueous solution was washed with dichloromethane (50 mL)
  4. customA precipitate formed
  5. stirringthe mixture was stirred for 1 hour
  6. customThe solid was isolated by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-e1706afcd750406ca94bf65f16080b80
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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