m-Chloroperbenzoic acid → 2-Methyl-5-(3-(4-(methylsulfinyl)phenyl)-1-benzofuran-5-yl)-1,3,4-oxadiazole

HRID 452723Notes

Reaction equation

HRID 452723 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]([S:21][CH3:22])=[CH:17][CH:16]=4)[C:11]=3[CH:23]=2)=[N:5][N:6]=1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[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]([S:21]([CH3:22])=[O:32])=[CH:19][CH:20]=4)[C:11]=3[CH:23]=2)=[N:5][N:6]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 444817562-Methyl-5-[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole

Product 1

HCID 248559582-Methyl-5-(3-(4-(methylsulfinyl)phenyl)-1-benzofuran-5-yl)-1,3,4-oxadiazoleYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-5-[3-[4-(methylthio)phenyl]-1-benzofuran-5-yl]-1,3,4-oxadiazole (322 mg, 1.00 mmol) in dichloromethane (10 mL) was added m-chloroperbenzoic acid (70%, 259 mg, 1.05 mmol) at room temperature, and the resulting mixture was stirred for 5 min. The reaction mixture was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (ethyl acetate) and recrystallized from tetrahydrofuran to give the title compound (284 mg, yield 84%) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by basic silica gel column chromatography (ethyl acetate)
  3. customrecrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-50b5d261ee1b496cbb1b272cf847ef23
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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