NOTES 557 ton and Overhoff state: "Very numerous attempts were made to condense phthalimidohalogenoacetones with ethyl sodiochloromalonate and indeed with ethyl sodiomalonate itself under various conditions, but all were in vain. The halogenoacetones reacted exothermically with the sodiomalonates with rapid elimination of the sodium halide, but normal condensation did not occur, the products consisting for the most part of highly pigmented resins."The coupling of III with sodium diethylmalonate was studied in several solvents under various conditions and was found to yield several products. At refluxing temperature in alcohol sodium bromide was formed, but attempts to crystallize a product from alcohol, ether, and chloroform failed. A very small amount of material was crystallized from acetone, but was not studied further. When III was added as a solid to an alcoholic solution of sodium diethylmalonate at room temperature the reaction mixture crystallized spontaneously.The material (obtained in high yield, but not the desired product) was recrystallized from 95% ethanol in which it is only slightly soluble, m.p. 278-279°. A sample was prepared for analysis by recrystallization from W,W-dimethylformamide by addition of water and also from alcohol-water.The analysis suggested phthalimide (calculated
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