Reactions of phosphorous oxychloride-amide adducts XIII A novel synthesis of 1-N,N-Dime-thylamino-1-ethoxyethylene

Meerwein et aL[1] succeeded in the preparation of l-N,N-dimethylamino-1-ethoxyethylene [1]. Bredereck and co-workers [2] obtained the ethoxyenamine from the reaction of N,N-dimethylacetamide- dimethylsulphate adduct with sodium ethoxide followed by distillation over calcium metal. Electrophilic addition to the double bond in the ethoxyenamine [1] has been reported. With acid chlorides, the enamine afforded the corresponding beta- ketoamides [3]. We would like to report a direct and simple method for the synthesis of the ethoxyenamine. This compound has now been prepared by the treatment of dimethylacetamide-ethyl chloroformate adduct [4] with triethylamine, whereby CO[2] is evolved