126 Scientific Proceedings^ Royal Dublin Society. 



urethane as were obtained under somewhat similar conditions from 2- or 4-nitro- 

 phenylure thane. 



The mononitro- and dinitro-echyl-phenyhirethanes were also obtained— the 

 latter in very small quantity— by the action of concentrated nitric acid on ethyl- 

 phenylurethane in a gently heated acetic acid solution. At the ordinary tempera- 

 ture and at low concentrations, nitric acid reacted very slowly and incompletely 

 with ethyl-phenylurethane in acetic acid solutions to which one or two equiva- 

 lents of the nitric acid had been added, and the product consisted, even after five 

 months standing, mainly, if not wholly, of the unchanged urethane. On the 

 other hand, from a solution to which three molecular c^uantities of nitric acid had 

 been added we were able to separate some 4-nitro-ethyl-phenylurethane, while 

 from solutions to which four or five molecular amounts of nitric acid bad been 

 added we separated in each case dinitro-ethyl-phenylurethane. The quantities 

 obtained, however, in all cases were small, the reactions in the cold acetic acid 

 solution being very incomplete, even when the reactions were allowed to go on for 

 a long period. 



The course of the reactions may be represented by the following scheme : — 



Ethyl-phenylurethane 

 (oil). 



Experimental. 

 A.— ACTION OF NITROGEN PEROXIDE ON ETHTL-PBENYLURETHANE. 



A rapid current of nitrogen peroxide fumes, generated by heating lead nitrate, 

 was passed for three hours through a solution of ethyl-phenylurethane in carbon 

 tetrachloride. The clear red-coloured solution thus obtained was allowed to stand 

 for twenty-four hours at the temperature of the laboratory. The solvent was re- 

 moved and the oily residue was washed, first with water, then with ether, and was 

 finally dissolved in boiling alcohol. In this way the reaction product was separated 

 into a less soluble crystalline body, melting at 88°-89° C, and a more soluble 

 crystalline substance, which melted at 56°-56°C. 



The crystalline substance, which melted at 55°-56" C, gave on analysis the 

 following results : — 



0"2076 g. of the substance gave 2r5 c.c. of moist nitrogen at 18° 0. and 750 mm., 



corresponding to N ll" 9. 

 CnHuNsOi requires N 11-85. 



