Thiophene-3-carboxylic acid → 4-[3-(3-Thiophenecarbonylamino)propylthio]pyridine

Participants

Reaction Steps

To a solution of 100 g (7.80mmol) of thiophene-3-carboxylic acid and 1.08 g 410.1 mmol) of N-hydroxysuccinimide in 70 ml of methylene chloride, 1.80 g (9.36 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 1 hour. Further, 1.31 g (7.80 mmol) of 4-(3-aminopropylthio)pyridine was added, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was washed with water and dried, and then the solvent was distilled off. The residue was purified by column chromatography (eluent: methanol/ethyl acetate=1:10) to obtain 1.65 g of the desired compound (yield: 76.1%, colorless powder). mp: 121.0°-122.0° C.

Provenance & Evidence