Decomposition N-nitrosohydroxyalkylureas and N-nitrosooxazolidones in aqueous buffer.

The decomposition of N-nitroso-2-hydroxyethylurea, N-nitrosooxazolidone, N-nitroso-2-hydroxypropylurea and N-nitroso-5-methyloxazolidone in pH 7.4 phosphate buffer was studied. The aldehydes and ketones formed in the decompositions were monitored through the formation of dinitrophenylhydrazine derivatives, which were then analysed by high-performance liquid chromatography. N-Nitroso-2-hydroxyethylurea gave a 25% yield of acetaldehyde dinitrophenylhydrazone, while N-nitrosooxazolidone gave only 2%. The major product from the latter is 1,3-dioxolane-2-one (ethylene carbonate); ethylene glycol is a major product from both. The other two compounds studied gave similar products, but in much lower yields.