m-Chloroperbenzoic acid → 5-Bromo-2-[(2,6-dichlorophenyl)methanesulfinyl]-1-oxo-1lambda~5~-pyridine

HRID 1980213Notes

Reaction equation

HRID 1980213 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:9][CH2:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[N+:6]([O-:8])[CH:7]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:9]([CH2:10][C:11]2[C:12]([Cl:18])=[CH:13][CH:14]=[CH:15][C:16]=2[Cl:17])=[O:27])=[N+:6]([O-:8])[CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 204023455-Bromo-2-{[(2,6-dichlorophenyl)methyl]sulfanyl}-1-oxo-1lambda~5~-pyridine

Product 1

HCID 134778795-Bromo-2-[(2,6-dichlorophenyl)methanesulfinyl]-1-oxo-1lambda~5~-pyridineYield 83.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2.3 g of 5-bromo-2-(2,6-dichlorobenzylthio)pyridine-N-oxide was dissolved in 50 ml of chloroform, and a solution of 1.6 g of metachloroperbenzoic acid (content: 70%) dissolved in 30 ml of chloroform was added dropwise thereto at 5° to 10° C. over 10 minutes. The mixture was stirred at 5° to 10° C. for an additional 2 hours. The resulting mixture was washed twice with potassium carbonate solution and dried over magnesium sulfate. The chloroform was evaporated, and the residue was recrystallized from benzene to obtain 2.0 g of 5-bromo-2-(2,6-dichlorobenzylsulfinyl)pyridine-N-oxide (Compound (2)). Yield, 83%. M.P., 187.5°-188.5° C.

Workup

  1. additionwas added dropwise
  2. washThe resulting mixture was washed twice with potassium carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. customThe chloroform was evaporated
  5. customthe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-3efb462294d0495582ae0fc3b71e2629
Source dataset
uspto-grants-1985_04
Patent number
US04508562

Reaction notes

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