m-Chloroperbenzoic acid → HCID 71714806, compound

HRID 520973Notes

Reaction equation

HRID 520973 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21][CH2:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:26]=[CH:27][CH:28]=1)(=[O:12])=[O:11].C1C=C(Cl)C=C(C(OO)=[O:41])C=1>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[S:10]([NH:13][C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=1[S:21]([CH2:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:26]=[CH:27][CH:28]=1)=[O:41])(=[O:11])=[O:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71714817HCID 71714817, compound

Product 1

HCID 71714806HCID 71714806, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{3-[({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)methyl]phenyl}acetamide (105 mg, 0.216 mmol) in CH2Cl2 (3 ml) was added mCPBA (52 mg, ˜0.216 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 (55 mg, 51%).

Workup

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

Sources & evidence

ORD record
ord-dc4f7d71aebc42c8a18cd5eff6c9ad1d
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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