m-Chloroperbenzoic acid → 2-Ethoxycarbonyl-5-(4-methylsulfinylphenyl)-1,3,4-oxadiazole

HRID 54558Notes

Reaction equation

HRID 54558 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=2)=[N:9][N:10]=1)=[O:5])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:24]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([S:17]([CH3:18])=[O:24])=[CH:15][CH:16]=2)=[N:9][N:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 545006572-Ethoxycarbonyl-5-(4-methylthiophenyl)-1,3,4-oxadiazole

Product 1

HCID 199591912-Ethoxycarbonyl-5-(4-methylsulfinylphenyl)-1,3,4-oxadiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-ethoxycarbonyl-5-(4-methylthiophenyl)-1,3,4-oxadiazole (0.7 g) in chloroform (14 ml), m-chloroperoxybenzoic acid (0.57 g) was added dropwise at 4°-6° C. with stirring. After 30 minutes, the reaction mixture was extracted with chloroform (50 ml), washed with a sodium iodide aqueous solution, a sodium thiosulfate aqueous solution, a sodium hydrogencarbonate aqueous solution and brine successively and dried over magnesium sulfate. After evaporating the solvent, the residue was crystallized from diethyl ether to afford 2-ethoxycarbonyl-5-(4-methylsulfinylphenyl)-1,3,4-oxadiazole.

Workup

  1. extractionthe reaction mixture was extracted with chloroform (50 ml)
  2. washwashed with a sodium iodide aqueous solution
  3. dry with materiala sodium thiosulfate aqueous solution, a sodium hydrogencarbonate aqueous solution and brine successively and dried over magnesium sulfate
  4. customAfter evaporating the solvent
  5. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-c3a90571910a454b930e177102155a97
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

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