Sodium methanethiolate → 2,5-Dichloro-4-methyl-6-(methylthio)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To a slurry of 2,5,6-trichloro-4-methyl-nicotinonitrile (10.0 g, 45.2 mmol, Tetrahedron, 1977, 33, 113-117) in MeOH (150 ml) at 0° C. is added solid sodium thiomethoxide (3.33 g, 45.2 mmol). The mixture is stirred at 0° C. for 1 hour, then room temperature for 1 hour. The reaction is quenched by the addition of water (250 ml). The mixture is partitioned between water and EtOAc (500 ml each), and the layers are shaken and separated. The organic layer is dried (anhydrous magnesium sulfate), filtered, and concentrated to give the title compound as a yellow solid (10.5 g, 99%). Mass (m/z): 233.0 (M++1).

Provenance & Evidence