Sodium Thiosulfate → HCID 68664496, compound

HRID 452786Notes

Reaction equation

HRID 452786 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][S:24][CH3:25])=[CH:17][CH:16]=4)[C:11]=3[CH:26]=2)=[N:5][N:6]=1.CN(C)C(=[O:31])C.ClC1C=CC=C(C(OO)=O)C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH3:1][C:2]1[O:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][S:24]([CH3:25])=[O:31])=[CH:19][CH:20]=4)[C:11]=3[CH:26]=2)=[N:5][N:6]=1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 31374DimethylacetamideHCID 70297m-Chloroperbenzoic acidHCID 686633502-Methyl-5-[3-[4-[2-(methylthio)ethoxy]phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

Product 1

HCID 68664496HCID 68664496, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 2-methyl-5-[3-[4-[2-(methylthio)ethoxy]phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (186 mg, 0.51 mmol), N,N-dimethylacetamide (2.5 mL) and acetonitrile (2.5 mL) was added m-chloroperbenzoic acid (122 mg, 0.51 mmol) at room temperature, and the resulting mixture was stirred for 2 hr. A saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was stirred for 30 min and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (53.0 mg, yield 27%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred for 30 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 magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=10/1-0/1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-0b222b0e4b694ec19504ef51bdb469b0
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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