Sodium Thiosulfate → HCID 68663384, compound

HRID 452841Notes

Reaction equation

HRID 452841 reaction equation
CS[C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[CH:9]=2)=[N:5][N:4]=1.Cl[C:26]1C=CC=C(C(OO)=O)C=1.[S:36]([O-:40])([O-])(=[O:38])=S.[Na+].[Na+]>CN(C)C(=O)C>[CH3:26][S:36]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:22])[F:23])[CH:16]=3)[CH:9]=2)=[N:5][N:4]=1)(=[O:40])=[O:38]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 68663950HCID 68663950, compound

Product 1

HCID 68663384HCID 68663384, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-[5-(methylthio)-1,3,4-oxadiazol-2-yl]-N-[3-(trifluoromethyl)phenyl]pyridin-2-amine (455 mg, 1.29 mmol) in N,N-dimethylacetamide (5 mL) was added m-chloroperbenzoic acid (70%, 619 mg, 2.58 mmol), and the resulting mixture was stirred at room temperature for 2 hr and at 50° C. overnight. A saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was stirred for 15 min and extracted with ethyl acetate. The organic layer was washed with 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 (hexane/ethyl acetate=9/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (126 mg, yield 25%) as yellow crystals.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-0cad309179b943e29569c1c6c7554cf0
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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