m-Chloroperbenzoic acid → HCID 71714804, compound

HRID 70466Notes

Reaction equation

HRID 70466 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:24]=2)=[C:6]([NH:8][S:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[CH:16]=2)(=[O:11])=[O:10])[CH:7]=1.C1C=C(Cl)C=C(C(OO)=[O:42])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:21]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])[CH:24]=2)=[O:42])=[C:6]([NH:8][S:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[CH:16]=2)(=[O:11])=[O:10])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71714815HCID 71714815, compound

Product 1

HCID 71714804HCID 71714804, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[5-chloro-2-({3-[(methylsulfonyl)amino]benzyl}sulfanyl)phenyl]-1-benzofuran-2-sulfonamide (124 mg, 0.237 mmol) in CH2Cl2 (5 ml) was added mCPBA (57 mg, ˜0.237 mmol) and the reaction was stirred at room temperature for 1 hour. The reaction mixture was directly loaded onto Celite and purified by flash column chromatography on silica gel (50-100% EtOAc in hexane) to yield the title compound (78 mg, 61%).

Workup

  1. custompurified by flash column chromatography on silica gel (50-100% EtOAc in hexane)

Sources & evidence

ORD record
ord-d5176479a6794f209e64db50522625d0
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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