Methyl iodide → Diethyl 2-(methylsulfanyl)-1H-imidazole-4,5-dicarboxylate

Participants

Reaction Steps

Iodomethane (15.62 g; 0.11 mol) was added to a solution of 24.4 g (0.10 mol) of the above-produced diethyl 2-mercapto-4,5-imidazole-dicarboxylate (24.4 g; 0.10 mol) and sodium methoxide (6.0; 0.11 mol) in absolute methanol (500 mL) at room temperature. Additional iodomethane (5 g) was added after 1 hour and the yellow solution was allowed to stir at room temperature for 3 hours. The methanol was then removed in vacuo, the residue was treated with cold water and the light yellow solid was filtered and dried to give diethyl 2-(methylthio)imidazole-4,5-dicarboxylate (22.3 g; 86%).

Provenance & Evidence