Hydrochloric Acid → 2-[(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetic acid

HRID 534817Notes

Reaction equation

HRID 534817 reaction equation
[CH:1]([C:3]1[C:4]([CH3:16])=[N:5][N:6]([CH3:15])[C:7]=1[S:8][CH2:9][C:10]([O:12]CC)=[O:11])=[O:2].[OH-].[Na+].CO.Cl>O1CCCC1>[CH:1]([C:3]1[C:4]([CH3:16])=[N:5][N:6]([CH3:15])[C:7]=1[S:8][CH2:9][C:10]([OH:12])=[O:11])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 63802037Ethyl [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetate

Product 1

HCID 470023932-[(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetic acidYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl [(4-formyl-1,3-dimethyl-1H-pyrazol-5-yl)sulfanyl]acetate obtained in Reference Example 2 (2.12 g), 8 M sodium hydroxide solution (5 mL), methanol (50 mL), and tetrahydrofuran (50 mL) was stirred at room temperature for 2 h. 6 M Hydrochloric acid solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate-diisopropyl ether to provide the title compound (1.09 g, 58%) as a solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-fd99a6f0705d4451a3c57a118e994a34
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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