Sodium Hydroxide → HCID 19996488, compound

Participants

Reaction Conditions

Reaction Steps

m-Chloroperbenzoic acid, 91% (1.13 g, 0.0059 mol) dissolved in CH2Cl2 (25 ml) and cooled to -10° C. was added under stirring to 4,6-dimethyl-5-heptyloxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-1H-benzimidazole (2.7 g, 0.0059 mol) dissolved in CH2Cl2 (50 ml) maintaining the temperature at -5° C. Stirring was continued at -5° C. for 10 min. The two phases were separated and then NaOH (0.26 g, 0.0066 mol) dissolved in water (50 ml) was added under vigorous stirring. The two phases were separated. The organic phase was dried (Na2SO4), filtered and the solvent evaporated off giving a residual oil, which according to NMR included 30% of unreacted starting material. The oil was chromatographed on a silica column using CH3OH--CH2Cl2 5:95 as eluant and then the product was recrystallized from CH3CN giving the desired product in crystalline form (0.85 g, 32%), m.p. 116° C.

Provenance & Evidence