Sodium Thiosulfate → HCID 66697820, compound

HRID 340596Notes

Reaction equation

HRID 340596 reaction equation
[F:1][C:2]1[C:7]([N:8]2[C:12](SC3C=CC=C(C)C=3)=[CH:11][C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([C:33](OO)=O)[CH:28]=1.[S:37]([O-:41])([O-])(=[O:39])=S.[Na+].[Na+]>C(OCC)(=O)C>[F:1][C:2]1[C:7]([N:8]2[C:12]([S:37]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH3:33])[CH:28]=3)(=[O:41])=[O:39])=[CH:11][C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 66697853HCID 66697853, compound

Product 1

HCID 66697820HCID 66697820, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of crude ethyl 1-(2-fluoropyridin-3-yl)-5-[(3-methylphenyl)sulfanyl]-1H-pyrazole-3-carboxylate (334 mg) in ethyl acetate (7.5 mL) was added 3-chloroperbenzoic acid (1.59 g). The mixture was stirred at room temperature for 3 hr, treated with saturated aqueous sodium thiosulfate solution, and extracted with ethyl acetate. The extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1) to give the title compound as a colorless oil (yield 384 mg, 2 steps yield 62%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=9:1→2:1)

Sources & evidence

ORD record
ord-4b627c3bfcbd477e97a6b363c3ea7aa2
Source dataset
uspto-grants-2014_11
Patent number
US08895588B2

Reaction notes

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