NEP. — BIVALENT CARBON. 159 



That in the above case au iutermediate formation of the imide- 



chloride 



C2H5N : CCl 

 I 

 O : COCgHg 



takes place was proved as follows. 5 c.cm. ethylisocyanide and 7.8 

 grams chlorocarbonic ether were heated for 6 hours at 6(>°-70°, 

 whereby a c()[)ious evolution of carbondioxide and of ethylchloride 

 takes place. The very dark residue was treated with absolute ether 

 and much polymerized ethylisocyanide separated out in brown flakes 

 The ethereal filtrate gave a small amount of an oil (free from chloro- 

 carbonic ether), which was warmed gently with lime water. After 

 getting rid of the excess of lime by means of carbonic acid, the filtrate 

 gave, on concentration, crystals of calcic ethyloxaminate, which sepa- 

 rated out in needles. The free ethyloxarainic acid obtained from this 

 salt melted at 123°, and was found identical in its properties (as well 

 as also the salt) with the previous statements of Wallach* The yield 

 of calcic ethyloxaminate is very poor, — never over 0.2 gram ; its 

 source can only be explained through the intermediate formation of 

 the imidechloride 



C2H5N • CCl 

 I 

 O : COC2H5 



in the above reaction this substance must necessarily, by saponifica- 

 tion, yield ethyloxamiiiic acid, 



C2H5N COH 

 I 

 O : COH. 



A better yield of the imidechloride could, in all probability, be ex- 

 pected on allowing molecular proportions of ethylisocyanide and 

 chlorocarbonic ether to stand at ordinary temperature for a week or 

 more. 



From the above experiments, it is clear that the aliphatic isocyano- 

 gen derivatives behave in a manner entirely analogous to the corre- 

 sponding aromatic derivatives, and differ from these only in the fact 

 that they react more energetically. It was further shown that carbon 

 tetrachloride reacts with ethylisocyanide at 180°, benzolsulphochloride 

 at 85°, benzylchloride at 120° ; it was not possible, however, to iso- 

 late any definite addition products. 



* Ann. Cliem (Liebig), CLXX-XIV. 68. 



