Hydrochloric Acid → Ethyl 3-ethoxy-3-iminopropionate hydrochloride

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Reaction Steps

Anhydrous hydrogen chloride (2.0 mol) is added to a mixture of ethyl cyanoacetate (1.0 mol) and ethanol (1.1 mol) in ethyl acetate (1 L) at 0° C. over a period of three hours. The mixture is then stirred at 5°-10° C. for ten additional hours. Removal of the solvent under reduced pressure gives the intermediate ethyl 3-ethoxy-3-iminopropanoate hydrochloride in a yield of about 90%. The appropriate o-aminophenol (1.0 mol) is added with vigorous stirring below 15° C. to a solution of ethyl 3-ethoxy-3-iminopropanoate hydrochloride (1.0 mol) in methanol and allowed to react for ten hours at less than 20° C. After removal of the methanol, the residue is extracted with acetone and the extract is concentrated and diluted with cold 2-propanol to precipitate the ethyl 2-benzoxazolylacetate intermediate (m.p. 50°-53° C.) which is collected by filtration in a yield of 85%. A mixture of the ethyl 2-benzoxazolylacetate (1.0 mol), a benzaldehyde compound (1.0 mol), piperidine (10 ml) and acetic acid (2.5 ml) in toluene (1 L) is refluxed with agitation for four hours while removing the water of reaction. The reaction mixture is then cooled and filtered to obtain the product. This general procedure may be used to prepare the following compounds:

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