Sodium Thiosulfate → HCID 68663351, compound

HRID 452691Notes

Reaction equation

HRID 452691 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12](SC)=[N:13][N:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.Cl[C:18]1C=CC=C(C(OO)=O)C=1.[S:28]([O-:32])([O-])(=[O:30])=S.[Na+].[Na+]>C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]([S:28]([CH3:18])(=[O:32])=[O:30])=[N:13][N:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 68662846HCID 68662846, compound

Product 1

HCID 68663351HCID 68663351, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(2,3-dihydro-1-benzofuran-5-yl)-5-(methylthio)-1,3,4-oxadiazole (0.50 g, 2.13 mmol) in acetonitrile (10 mL) was added m-chloroperbenzoic acid (70%, 1.51 g, 6.40 mmol) at 0° C., and the obtained mixture was stirred at room temperature for 2 days. A saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1) to give the title compound (0.44 g, yield 78%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-78cf6d46426e4ee3ba51b72c90422b03
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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