BARTOW AND MCFARLAND : LIQUID AMMONIA. 83 



ethyl esters which was available was chlorpropionic ethyl ester. 

 Thus far the only product obtained from this ester has shown a melt- 

 ing-point of 72°, which is lower than that assigned to chlorpropion- 

 amid, (80"), by Beckurts-Otto (B. 9, 1592). 



From the foregoing, it appears that the presence of chlorin or 

 cyanogen in the alkyl radical aids in the formation of amids, while 

 the weaker halogen bromin generally causes the compound to break 

 up with the formation of ammonium bromid and decomposition prod- 

 ucts. We have tried, also, the action of a few esters in which the 

 hydrogen of the alkyl is substituted by an organic radical. These 

 radicals do not seem to aid in amid formation. From ijhenylacetic 

 ethyl ester we have obtained no results. From benzoylacetic ethyl 

 ester a small amount of a substance was obtained, which melted at 

 167°. This substance is apparently not identical with the benzoyl- 

 acetamid of Obriga (A. 266, 232), which melted at 113°. 



Acetacetic acid ethyl ester gave a white crystalline substance, 

 which, as the temperature rose to that of the room, quickly liquified, 

 forming a yellow oil. This is undoubtedly the same substance men- 

 tioned by Collie (A. 226, 298), who says that at 0° acetacetic acid ethyl 

 ester absorbs dry ammonia gas directly, forming an unstable addition 

 product, CeHioOsNHs, which quickly goes over into amidocrotonic 

 acid ethyl ester, CeHnNO-i. 



From the esters of dibasic acids, there were available those of ox- 

 alic, malonic, succinic and tartaric acids. Two of these only, oxalic 

 and tartaric, gave amids by the above method. The oxamid formed 

 very readily as a white, crystalline powder. It did not melt when 

 heated to 200°, but sublimed at higher temperatures. From tartaric 

 acid ethyl ester, after two treatments with ammonia, a small quantity 

 of a substance, melting at 166°, was obtained. We can find no au- 

 thority for a melting-point of tartramid. 



The action of ammonia on the ethyl esters of lactic, laevulinic and 

 citric acids was also investigated. None of these seemed to be 

 changed by the treatment, except that the citric acid ester became 

 slightly blackened. 



Four esters of aromatic acids were tried, ethyl benzoate, methyl 

 benzoate, ethyl phthalate, and ethyl salicylate. Of these the phthalic 

 ester gave a white crystalline compound, which melted at 175°. The 

 melting-point of j^hthalamid, according to Billow (A. 236, 188), is 219°. 



Four other esters have been treated in this manner. Two of them, 

 orthoformic acid ethyl ester and ethyl carbonate, showed no change, 

 but with ethyl chlorcarbonate a vigorous reaction took place ; dense 

 white fumes were formed, and a considerable quantity of an amor- 

 phous white substance was left in the vessel. This did not melt 



