Methanol → 2-Methoxy-5-(5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid methyl ester

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Reaction Steps

Treat a solution of 2-methoxy-5-(5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid (6.66 g, 26.5 mmol) and methanol (80 mL) under argon via syringe dropwise with thionyl chloride (2.9 mL, 40 mmol). Stir for three days and remove the methanol in vacuo. Purify the residue by flash chromatography (silica gel, 9.5×12.7 cm) eluting with 40% ethyl acetate in dichloromethane and then with ethyl acetate. Concentrate the desired fractions in vacuo to afford 4.55 g of 2-methoxy-5-(5-thioxo-1,5-dihydro-[1,2,4]triazol-4-yl)-benzoic acid methyl ester.

Provenance & Evidence