1. K. and M. A. Phelps — Preparation of Acetamide. 429 



Art. XXXIX. — The Preparation of Acetamide by the Action 

 of Ammonium Hydroxide and Ethyl Acetate ; by I. K. and 

 M. A. Phelps. 



[Contributions from the Kent Chemical Laboratory of Yale Univ. — clxv.] 



It has been stated by Hofmann* that the action of aqueous 

 ammonia upon ethyl acetate at ordinary temperatures yields 

 after several clays' standing considerable amounts of acetamide, 

 but that the amount of acetamide by no means corresponds to 

 the amount of ethyl acetate taken. Hofmann further states 

 that according to a communication from Dr. Bannow the yield 

 of acetamide, even when formed in large quantities, is usually 

 not much above 70 per cent of that theoretically demanded. 

 In this same communication Hofmann makes a similar state- 

 ment in regard to the action of ethyl formate. • 



In a former paper from this laboratoryf conditions have 

 been shown under which very nearly the theoretical yield of 

 formamide by the action of ammonium hydroxide and ethyl 

 formate is obtained. JSTow it has been found that conditions 

 closely similar will give theoretical yield as well in the case of 

 ethyl acetate and aqueous ammonia. 



For the work given here ethyl acetate of commerce was 

 treated in a separating funnel with sodium carbonate solution, 

 and, after separating from this, w T as washed with distilled 

 water. The ethyl acetate thus purified from acid impurities 

 was separated as completely as possible from the water, dried 

 over fused calcium chloride and then treated again with a fresh 

 portion of fused calcium chloride before fractioning. Portions 

 boiling between 77° and 77°*2 were taken as pure ethyl acetate. 



Definite portions of the pure ethyl acetate were weighed, 

 and, after chilling below zero in an ice and salt mixture, were 

 mixed in a stoppered reagent bottle with definite volumes of 

 ammonium hydroxide. In some of these experiments the 

 ammonium hydroxide was the pure concentrated ammonium 

 hydroxide of commerce ; in others the ammonium hydroxide 

 was made more concentrated by saturating at —10° the pure 

 concentrated ammonium hydroxide of commerce with dry 

 ammonia gas obtained by heating concentrated ammonium 

 hydroxide in a flask connected with a return condenser and 

 drying further the ammonia by passing it through a lime 

 tower ; while in a third series of experiments the product 

 obtained by mixing in the cold in a stoppered reagent bottle 

 the ethyl acetate and ammonium hydroxide was saturated in 

 the cold with dry ammonia gas obtained in the manner given 



* Berichte, xv, 977. \ This Journal, xxiv, 173. 



