m-Chloroperbenzoic acid → 6-Chloro-pyridine-3-sulfonic acid[3-chloro-4-(naphthalene-2-sulfinyl)-phenyl]-amide

HRID 1865503Notes

Reaction equation

HRID 1865503 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][S:20]([C:23]2[CH:24]=[N:25][C:26]([Cl:29])=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1.ClC1C=C(C=CC=1)C(OO)=[O:35]>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][S:20]([C:23]2[CH:24]=[N:25][C:26]([Cl:29])=[CH:27][CH:28]=2)(=[O:22])=[O:21])[CH:5]=[CH:6][C:7]=1[S:8]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)=[O:35]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 235152236-Chloro-pyridine-3-sulfonic Acid [3-Chloro-4-(naphthalen-2-ylsulfanyl)phenyl]-amide

Product 1

HCID 235152246-Chloro-pyridine-3-sulfonic acid[3-chloro-4-(naphthalene-2-sulfinyl)-phenyl]-amideYield 30%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-Chloro-pyridine-3-sulfonic acid [3-chloro-4-(naphthalen-2-ylsulfanyl)-phenyl]-amide (94, 55 mg, 0.12 mmol) in CH2Cl2 (2 mL), was added dropwise a solution of m-chloroperoxybenzoic acid (mCPBA, Aldrich, 36 mg, 0.2 mmol) in CH2Cl2 (1 mL). The resulting mixture was stirred at ambient temperature for 1 hour and diluted with EtOAc (60 mL). The organic layer was washed with saturated aqueous NaHCO3 solution (50 mL), twice with brine solution (50 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was chromatographed (10-25% EtOAc in hexane) to yield 17 mg (30%) of 103 as an off white solid.

Workup

  1. washThe organic layer was washed with saturated aqueous NaHCO3 solution (50 mL), twice with brine solution (50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe crude solid was chromatographed (10-25% EtOAc in hexane)

Sources & evidence

ORD record
ord-4ceed392dcad4c2a8e39aed390b88c57
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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