3-Hydroxypicolinamide → 3-Hydroxythiopicolinamide

Participants

Reaction Steps

A suspension of 3-hydroxypicolinamide (1 g) and Lawesson's reagent (2 g) in dry dioxane (75 ml) was allowed to react under Argon atmosphere at 95° C. for 4 hours. Then, insoluble solids in the reaction mixture was filtered off with suction and the filtrate was concentrated. The residue was dissolved in methylene chloride and purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1). The second yellow fraction was concentrated. the residual solids were recrystallized from CHCl3 -n-hexane to give yellow crystals of 3-hydroxythiopicolinamide (546 mg, 46%), m.p. 150°-151° C.

Provenance & Evidence