m-Chloroperbenzoic acid → N-(1-{5-[(4-ethoxybenzyl)sulfinyl]-1-benzofuran-2-yl}ethyl)acetamide

HRID 1888770Notes

Reaction equation

HRID 1888770 reaction equation
[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][S:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:15][C:14]=3[CH:24]=2)=[CH:6][CH:5]=1)[CH3:2].ClC1C=CC=C(C(OO)=[O:35])C=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:1]([O:3][C:4]1[CH:26]=[CH:25][C:7]([CH2:8][S:9]([C:10]2[CH:11]=[CH:12][C:13]3[O:17][C:16]([CH:18]([NH:20][C:21](=[O:23])[CH3:22])[CH3:19])=[CH:15][C:14]=3[CH:24]=2)=[O:35])=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58047107N-(1-[5-[(4-ethoxybenzyl)sulfanyl]-1-benzofuran-2-yl]ethyl)acetamide

Product 1

HCID 58047301N-(1-{5-[(4-ethoxybenzyl)sulfinyl]-1-benzofuran-2-yl}ethyl)acetamideYield 25%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(1-[5-[(4-ethoxybenzyl)sulfanyl]-1-benzofuran-2-yl]ethyl)acetamide (100 mg, 0.271 mmol) obtained in Example 49 in ethyl acetate (2 mL) was added 75% m-chloroperbenzoic acid (79.8 mg, 0.324 mmol), and the mixture was stirred at room temperature for 1.5 hr. Aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted twice with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to ethyl acetate), and the obtained solid was washed with diethyl ether to give the title compound (25.5 mg, yield 25%).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to ethyl acetate)
  6. washthe obtained solid was washed with diethyl ether

Sources & evidence

ORD record
ord-25d62dcc58c543c0b64868d1a1a17aaa
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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