Sodium Thiosulfate → HCID 67272364, compound

HRID 1696184Notes

Reaction equation

HRID 1696184 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:24]=[C:25](SC)[C:26]=2[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=1.Cl[C:35]1C=CC=C(C(OO)=O)C=1.[S:45]([O-:49])([O-])(=[O:47])=S.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[N:10][C:11]2[N:12]([N:24]=[C:25]([S:45]([CH3:35])(=[O:49])=[O:47])[C:26]=2[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 67272916HCID 67272916, compound

Product 1

HCID 67272364HCID 67272364, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2-chlorophenyl)-3-ethoxycarbonyl-7-(4-trifluoromethyl-phenyl)-2-methylthiopyrazolo[1,5-a]pyrimidine (compound obtained in Reference Example A5; 11.0 g) in methylene chloride (400 mL) was added m-chloroperbenzoic acid (16.5 g) at 0° C., and the mixture was stirred at room temperature for 3 hours. To the reaction mixture was added dropwise an aqueous sodium thiosulfate solution at 0° C. under stirring, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo, and the resultant crude product was washed with ethanol to give 6-(2-chlorophenyl)-3-ethoxycarbonyl-7-(4-trifluoromethylphenyl)-2-methylsulfonylpyrazolo[1,5-a]pyrimidine (10.7 g, yield: 91%) as a powder.

Workup

  1. stirringunder stirring
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. washthe resultant crude product was washed with ethanol

Sources & evidence

ORD record
ord-8e072d64ca614474afa04a4f26da5ef9
Source dataset
uspto-grants-2012_04
Patent number
US08163759B2

Reaction notes

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