m-Chloroperbenzoic acid → HCID 71714791, compound

HRID 70467Notes

Reaction equation

HRID 70467 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]([OH:25])=[O:24])(=[O:12])=[O:11].C1C=C(Cl)C=C(C(OO)=[O:34])C=1>C(Cl)Cl.C(#N)C>[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]([OH:25])=[O:24])=[O:34])(=[O:11])=[O:12]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 71714798HCID 71714798, compound

Product 1

HCID 71714791HCID 71714791, compoundYield 74.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ({2-[(1-benzofuran-2-ylsulfonyl)amino]-4-chlorophenyl}sulfanyl)acetic acid (44 mg, 0.11 mmol) in CH2Cl2 (2 ml) and acetonitrile (2 ml) was added mCPBA (27 mg, ˜0.11 mmol). The reaction was stirred at room temperature for 4 hours and was concentrated. The residue was purified by flash column chromatography on silica gel (50-100% EtOAc in hexane, then 20-30% MeOH in EtOAc) followed by PTLC (25% MeOH in EtOAc) to yield the title compound (34 mg, 74%).

Workup

  1. concentrationwas concentrated
  2. customThe residue was purified by flash column chromatography on silica gel (50-100% EtOAc in hexane

Sources & evidence

ORD record
ord-04bb3a952b4e4e38a255b8252fc4ff08
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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