Faculty Sponsor
James Bashkin
Final Abstract for URS Program
The purpose of my research project is to utilize green chemistry principles to synthesize an intermediate for Glutethimide, a drug used to treat patients with insomnia. Many pharmaceutical processes require the use of halide-containing chemicals which are harmful to the environment when discarded as waste. Not only does this waste affect the quality of drinking water and aquatic life, but it affects the economy as well. The cost of waste disposal increases with the increasing difficulty of treating it and thus raises the cost of production for pharmaceutical companies.
The reaction of choice is a nucleophilic aromatic substitution of hydrogen, or NASH, reaction. This would, ideally, replace any halide-containing starting materials with a less harmful substitute and would result in less toxic waste runoff.
Two reactions utilizing 1-chloro-4-nitrobenzene were carried out to be used as analytical standards. For the green reactions, instead of using the halide-containing nitrobenzene, regular nitrobenzene was used and was reacted with methyl-cyanoacetate and a base to attempt to generate the desired compound. Dimethylformamide (DMF) is a commonly used solvent for this synthesis but was replaced with dimethylsulfoxide (DMSO). A series of reactions were run with different variables changed such as the temperature of the reaction and the base used. The desired product was not formed for the reactions in which the temperature was changed and potassium carbonate (K2CO3) was used as a base, however, when potassium hydroxide (KOH) was used as a base and the reaction was run at room temperature, a noticeable color change similar to that of the standard reaction was observed. NMR and ES-MS tests were conducted to confirm that the product was created, and characteristic peaks of the desired compound were identified. A workup procedure was used with the intention of improving the purity of the compound, but it was determined that purifying the compound to obtain a final yield would be challenging. Future research would include finding methods to effectively purify and isolate the compound as well as finding other viable replacements for DMF such as Cyrene and other Cyrene mixes. It would also include carrying out more reactions with KOH and similar bases.
Presentation Type
Visual Presentation
Document Type
Article
Publication Date
April 2023