Hydrochloric Acid → 3-(Methylthio)-6-phenyl-5-(pyridin-3-yl)-1,2,4-triazine

Participants

Reaction Steps

To a suspension of 2-(hydroxyimino)-1-phenyl-2-(pyridin-3-yl)ethanone (0.434 g, 1.918 mmol) in a 1:1 mixture of EtOH/H2O (8.0 mL) was added hydrazinecarbothioamide (0.262 g, 2.88 mmol) followed by concentrated HCl (0.307 mL, 3.84 mmol). The reaction was stirred at room temperature for 1 h then heated to 90° C. overnight. Upon completion, the reaction mixture was neutralized with saturated NaHCO3. The solid formed was filtered and rinsed with H2O. The solid was added to a solution of potassium carbonate (1.326 g, 9.59 mmol) in H2O (50 mL) and heated to 90° C. overnight. Upon completion, the reaction mixture was cooled to room temperature then placed in an ice bath. To the ice cooled mixture was added iodomethane (0.119 mL, 1.918 mmol). The reaction was stirred at 0° C. and slowly warmed to room temperature. After stirring overnight, the solution was extracted with CH2Cl2 (3×75 mL), washed with H2O, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow solid (0.152 g). LCMS m/z=281.1 [M+H]+.

Provenance & Evidence