m-Chloroperbenzoic acid → HCID 501200, compound

HRID 2300992Notes

Reaction equation

HRID 2300992 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][S:10]([C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:19])=[O:11].ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:9][S:10]([C:12]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][N+:13]=1[O-:19])(=[O:28])=[O:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 501201HCID 501201, compound

Product 1

HCID 501200HCID 501200, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 8.0 g (0.03 mole) of 2[(2,6-dichlorophenyl)methylsulfinyl]-3-methyl-pyridine-N-oxide (See Example 29 above) in 150 ml of chloroform were added 10 g (0.05 mole) of metachloroperbenzoic acid. The mixture was stirred at room temperature for 24 hours, and then was washed with 20% K2CO3, and then with aqueous NaHSO3 until no peroxides were present. The chloroform layer was dried with Na2SO4 and then the mixture was filtered and the solvent removed on a steam bath. The residue was taken up in ether and filtered to give 2 g of solid, having a melting point of 215-218° C. The elemental analysis for C,H,N; the infrared, and the NMR all supported the proposed structure.

Workup

  1. washwas washed with 20% K2CO3
  2. dry with materialThe chloroform layer was dried with Na2SO4
  3. filtrationthe mixture was filtered
  4. customthe solvent removed on a steam bath
  5. filtrationfiltered

Sources & evidence

ORD record
ord-44bc5eba51664fb2963cb77e26e6f8b6
Source dataset
uspto-grants-2002_12
Patent number
US06498254B1

Reaction notes

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