Reagent development for the preparation of acid chloride for synthesis of bioactive compound

Abstract

The methodology for the preparation of acid chloride utilizing halogenated reagent and triphenylphosphine was thoroughly explored. Trichloroacetamide coupled with triphenylphosphine was turned out to be an effective reagent for this kind of transformation. A series of experiment to optimize the reaction conditions including type of halogenated reagent, type of base, solvent system, temperature and reaction time was cautiously conducted. The acid chloride generated could be successfully trapped with amine or alcohol yielding amides and esters, respectively. This methodology was applicable for aromatic and short chain aliphatic carboxylic acids. In addition, the application of this developed protocol for the synthesis of amides and esters was fruitfully accomplished. Eleven biologically active amides and five bioactive esters were prepared according to this method with the yield higher or comparable to those cited in literature.