m-Chloroperbenzoic acid → HCID 23331770, compound

HRID 224663Notes

Reaction equation

HRID 224663 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][C:12]([C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:11]2[CH3:24])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)Cl>[C:1]1([S:7]([CH2:8][CH2:9][N:10]2[C:14]([CH3:15])=[CH:13][C:12]([C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:11]2[CH3:24])=[O:33])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12603265HCID 12603265, compound

Product 1

HCID 23331770HCID 23331770, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 15 ml of methylene chloride was dissolved 589 mg (1.76 mmoles) of 2-(3-benzoyl-2,5-dimethylpyrrol-1-yl)ethyl phenyl sulfide, and 350 mg (1.72 mmoles) of m-chloroperbenzoic acid (85% purity) was added. The mixture was stirred at room temperature for 16 hours. The organic layer was washed with a 1.0 N aqueous solution of sodium hydroxide, and then water, dried, and concentrated, and chromatographed on a column of silic gel using benzene/ethyl acetate as an eluent to afford compound (410)(562 mg, 1.60 mmoles, 91%).

Workup

  1. additionwas added
  2. washThe organic layer was washed with a 1.0 N aqueous solution of sodium hydroxide
  3. dry with materialwater, dried
  4. concentrationconcentrated
  5. customchromatographed on a column of silic gel

Sources & evidence

ORD record
ord-b35c5c2b2a58479b9442097cbb3533ac
Source dataset
uspto-grants-1980_11
Patent number
US04233309

Reaction notes

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