18-Crown-6 → [1-(2-Azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester

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Reaction Steps

11 g. of the ethyl ester product from part (c) are added to acetone along with 5.7 g. of tetramethylguanidinium azide and 0.05 g. of 18-Crown-6. The mixture is refluxed for eight hours. After distilling off the solvent, the reaction mixture is stirred with 50 ml. of methylene chloride. The organic phase, after drying and concentrating, leaves an oil which crystallizes in the form of white crystals upon the addition of a small amount of isopropanol to yield [1-(2-azidoethyl)-2-(phenylmethylene)hydrazino]oxoacetic acid, ethyl ester; m.p. 59°-61°.

Provenance & Evidence