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

HRID 1980212Notes

Reaction equation

HRID 1980212 reaction equation
[Cl: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>[Cl: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 134778775-Chloro-2-{[(2,6-dichlorophenyl)methyl]sulfanyl}-1-oxo-1lambda~5~-pyridine

Product 1

HCID 134778785-Chloro-2-[(2,6-dichlorophenyl)methanesulfinyl]-1-oxo-1lambda~5~-pyridineYield 95.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

3.2 g of 5-chloro-2-(2,6-dichlorobenzylthio)pyridine-N-oxide was dissolved in 50 ml of chloroform, and a solution of 2.5 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 recyrstallized from 1:1 benzene-hexane to obtain 3.2 g of 5-chloro-2-(2,6-dichlorobenzylsulfinyl)pyridine-N-oxide (Compound (1)). Yield, 95%. M.P., 176.5°-177.5° 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

Sources & evidence

ORD record
ord-e318edc09b5f46e3a7269e0db2140bd7
Source dataset
uspto-grants-1985_04
Patent number
US04508562

Reaction notes

Loading…