1,1-Dimethylhydrazine → N-(1'-methoxycarbonyl-ethyl)-N-(N',N'-dimethyl-hydrazinoacetyl)-2,6-dimethylaniline

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Reaction Steps

18 g (0.3 mol) of N,N-dimethylhydrazine is added at room temperature to 28.4 g (0.1 mol) of N-(1'-methoxycarbonyl-ethyl)-N-chloroacetyl-2,6-dimethylaniline in 150 ml of toluene. The reaction mixture is then stirred at 50°-60° C. for 96 hours. After cooling to room temperature, there is added about 100 ml of 1 N sodium hydroxide solution, and the organic phase is separated. The aqueous solution is extracted with toluene, the toluene solutions are combined, and washed once with water. After being dried with sodium sulfate, the toluene solution is concentrated in a water-jet vacuum. The brown oil remaining is taken up in petroleum ether, whereupon the product crystallises and is filtered off. The petroleum ether solution is concentrated by evaporation to leave 7.7 g of product in the form of brown oil; nD21 =1.5272.

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