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

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Reaction Steps

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).

Provenance & Evidence