Sodium methanethiolate → 5-Methyl-6-(methylthio)nicotinonitrile

Participants

Reaction Steps

To a stirred suspension of sodium thiomethoxide (1.66 g, 23.71 mmol) in 2-propanol (20 mL) at room temperature under a nitrogen atmosphere was added a suspension of 6-fluoro-5-methyl-3-pyridinecarbonitrile (2.69 g, 19.76 mmol) in 2-propanol (10 mL). After one hour stirring at room temperature, TLC (25% EtOAc/hexane) indicated loss of starting material. The reaction mixture was diluted with water (20 mL) and filtered. The filtrate was extracted twice with ether (25 mL×2). The organic layers were combined, washed with water and evaporated in vacuo to give the desired product (2.57 g, 79.1%) as yellow fluffy crystals.

Provenance & Evidence