m-Chloroperbenzoic acid → HCID 22394144, compound

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Reaction Steps

A suspension of 4.0 g (15 mMol) of 3-[(1H-benzimidazol-2-yl)thiomethyl]-2-pyridinamine hemihydrate (see Example 79) in 50 ml of dichloromethane was cooled in an ice bath. A solution of 3.0 g (15 mMol) of ca. 85% m-chloroperbenzoic acid in the minimum amount of dichloromethane needed to form a solution was then added dropwise with stirring. After addition was complete, another 3.0 g of ca. 85% m-chloroperbenzoic acid was added. The reaction was quenched with 10 drops of dimethylsulfide. The mixture was washed with saturated aqueous sodium bicarbonate. The organic phase was concentrated in vacuo and chromatographed on silica gel (using ethanol-dichloromethane-triethylamine as eluent). Initial fractions yielded 249 mg of the title sulfone. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis. Anal. Calc'd. for C12H12N4SO2 : C, 54.15; H, 4.19; N, 19.43. Found: C, 53.79; H, 4.09; N, 19.29.

Provenance & Evidence