m-Chloroperbenzoic acid → 2-[(2,4-Dichlorophenyl)methanesulfinyl]-1-oxo-1lambda~5~-pyridine

HRID 1657337Notes

Reaction equation

HRID 1657337 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=1[O-:17].C1C=C(Cl)C=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][S:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=1[O-:17])=[O:26]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 470955022-{[(2,4-Dichlorophenyl)methyl]sulfanyl}-1-oxo-1lambda~5~-pyridine

Product 1

HCID 544932542-[(2,4-Dichlorophenyl)methanesulfinyl]-1-oxo-1lambda~5~-pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A well stirred solution of 5.8 gms (0.02 mole) of 2-(2,4-dichlorophenylmethylthio)pyridine N-oxide in 50 ml of chloroform is treated at 0° - 10° with 4 gms (0.02 mole) MCPBA (85%) in 50 ml of chloroform. The mixture is allowed to rise to ambient and held for 16 hours. The reaction mixture is washed with saturated sodium bicarbonate, dried and evaporated to 5.5 gms (89% theory) of product. Melting point 138° - 141°C. Structure confirmed by IR and NMR. (IR N-O 1240 cm-1, SO 1050 cm-1).

Workup

  1. washThe reaction mixture is washed with saturated sodium bicarbonate
  2. customdried
  3. customevaporated to 5.5 gms (89% theory) of product

Sources & evidence

ORD record
ord-b4804441c84f46c4aabd1252c1984a2c
Source dataset
uspto-grants-1976_06
Patent number
US03960542

Reaction notes

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