CHED 501 |
| Vancomycin is a front line antibiotic for treatment of life-threatening gram-positive bacterial infections and many clinical isolates have become resistant to it, focusing interest on successors to vancomycin. The purpose of this paper is to report the synthesis of diphenyl ether derivatives carried out by undergraduate science students majoring in forensic science and biology. Diphenyl ethers are structural elements found in medicinally useful antibiotics such as vancomycin as well as in biological toxins in the environment such as dioxins. The reported derivatives of diphenyl ethers serve as intermediates in the synthesis of these biologically active molecules. Commercially available p-cresol was converted into its potassium salt by heating with potassium hydroxide pellets and then reacted with p-chloronitrobenzene in the presence of copper and potassium iodide as catalyst, and DMF as a solvent under refluxing conditions to yield 4-methyl-4'-nitrodiphenyl ether as a product. The resulting product was chlorosulfonated regioselectively at the 2-position with chlorosulfonic acid at 0° C to yield the corresponding sulfonyl chloride derivative which was then further reacted with ammonium hydroxide under refluxing conditions to yield the corresponding sulfonamide derivative. |
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General Papers
8:00 AM-11:45 AM, Thursday, 14 September 2006 San Francisco Marriott -- Salon 10, Oral
Division of Chemical Education |