Sydnones were first synthesized in Sydney, Australia in 1935. When Earl and Mackney treated N-nitroso-N-phenylglycine with acetic anhydride they obtained a novel anhydrous derivative containing both a (+) and (-) charge. Slightly modified analogues of this proposed structure were later synthesized, resulting in a set of structures popularly termed 'sydnones' by virtue of their discovery in Sydney, Australia. All of these aromatic zwitterionic structures include two nitrogens, two carbons, and one oxygen atom within a 5-membered sydnone ring. Novel sydnones are of interest mainly for their biological activity. The first step of a typical 3-step sydnone synthesis involves aniline reacting with either bromoacetic acid or chloroacetic acid and sodium acetate, resulting in N-phenylglycine. This undergraduate research project involves the investigation of the "best" method for synthesizing various N-phenylglycine derivatives. This first synthetic step is typically heated at 60 degrees Celsius for 14.5 hours. Newly purchased HBN Smart Plugs and an Ipad are being employed to control the starting and stopping of the heating process. This investigation compares chloroacetic acid or bromoacetic acid reacting with either aniline, p-bromoaniline, or p-chloroaniline. Comparing the yields, cost, and product purity will help decide which synthetic method is 'best'.

Investigations into the synthesis of N-phenylglycine derivatives

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