Synthesis of Carboxylic Acid Derivatives

A mixture of carboxylic acid 27, thionyl chloride, and DMF in absolute toluene was stirred at room temperature for 10 min; after that, the appropriate amine was added and heated at reflux. Toluene and excess thionyl chloride were removed under reduced pressure. The crude product was washed 3 times with toluene to obtain powdered product. The resulting product was separated by column chromatography on SiO₂ using dichloromethane/methanol as eluent.

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Perin N., Gulin M., Kos M., Persoons L., Daelemans D., Fabijanić I., Stojković M.R, & Hranjec M. (2024). Synthesis and Biological Evaluation of Novel Amino and Amido Substituted Pentacyclic Benzimidazole Derivatives as Antiproliferative Agents. International Journal of Molecular Sciences, 25(4), 2288.

Publication 2024

Corresponding Organization : University of Zagreb

Other organizations : Rega Institute for Medical Research, KU Leuven, Rudjer Boskovic Institute

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Variable analysis

independent variables

Carboxylic acid 27
Thionyl chloride
Amine

dependent variables

Powdered product

control variables

Absolute toluene
Room temperature
Reflux temperature
Reduced pressure
Toluene washing
Column chromatography on SiO2 using dichloromethane/methanol as eluent

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