Ionic Liquid-assisted Synthesis of Celexocib Using Tris-(2-hydroxyethyl) Ammonium Acetate as an Efficient and...

Celecoxib is classified as none traditional nonsteroidal anti-inflammatory drugs (NSAIDs). This compound has conventional properties of NSAIDs such as anti-inflammatory, analgesic, and antipyretic activities beside reduced risk of gastrointestinal side effect of traditional NSAIDs such as ibuprofen. This compound gets a second sale rank of NSAIDs market at 2016 in the world and sales more than 17000 Kg in Iran during the past 6 month. So, a simple, rapid and green method for synthesis of this compound is important. In the present study, a novel green method was suggested for the synthesis of celecoxib using the ionic liquid. Celecoxib was provided by the reaction of trifluoroacetone, 4-methylbenzoylchloride, and 4-hydrazinobenzenesulfonamide hydrochloride. The tris-(2-hydroxyethyl) ammonium acetate as ionic liquid was prepared by mixing tris-(2-hydroxyethyl) ammonium and acetic acid, and used as an efficient catalyst. The structure of the synthetic products was confirmed by analytical and spectroscopic methods including ¹HNMR, ¹³CNMR, IR, MS and elemental analysis. This ionic liquid can play dual roles in the synthesis of celecoxib, as a catalyst to improve electrophilicity of carbonyl group and also as a solvent of reaction. The reaction rate and yield (86%) were improved considerably. Moreover IL showed the same efficiency when used in 4 consecutive reactions.