Ethyl iminoacetate hydrochloride

Dry hydrogen chloride is passed into an ice-cooled mixture of 41 g. (1.02 moles) of acetonitrile, 51 g. (1.1 moles) of absolute ethanol (p. 142), and 36 ml. of dry ether until 40 g. (1.1 moles) has been absorbed. The resulting mixture is allowed to stand at 0° for 2 hours and then is cooled to —30° in a Dry Ice bath. The precipitated solid is filtered off and dried first over potassium hydroxide and then over phosphorus pentoxide in a vacuum desiccator. The product is triturated with cold ( — 40°) anhydrous ether and again filtered and dried as before. The product is obtained in 85-95% yield. 

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A soln. of ethyl carbazate in abs. ethanol added dropwise at 0-10° to a stirred ice-salt-cooled soln. of ethyl iminoacetate hydrochloride in the same solvent, and the product isolated after 4 hrs. stirring below 10° ethyl acetate carbethoxyhydrazone (Y 10%) heated 1 hr. at 150° with excess aniline 3-hydroxy-4-phenyl-5-methyl-l,2,4-triazole (Y 10%). F. e. s. M. Pesson, S. Dupin, and M. Antoine, G. r. 253, 285 (1961). 

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