Ryan and Egan — The Action of Nitrous Acid, ^c, on Ur ethanes. 173 



which 6 molecular amounts of butyl nitrite and glacial acetic acid had been 

 added, quickly acquired a dark brown colour. After a month the solvent 

 was distilled under reduced pressiire, and the residue was washed with water 

 and dried. The solid was shaken with ether and filtered. It melted at 

 133° C, and proved to be ^.-nitro-diiihcnylnitrosamine. The ethered filtrate 

 left on evaporation a brown impure mixture of crystals, which melted over a 

 wide range of temperature, from 60° to 120° C, but whose constituents 

 could not be separated by fractional crystallisation from alcohol and carbon 

 tetrachloride. 



SUMSIAET. 



1. Ifitrous acid, unlike nitric acid, has no apparent nitrating action on 

 diphenylurethane, phenylbenzylurethane, ethylphenylurethane, ethyl-o-tolyl- 

 urethane, or pheuylbeuylether, at the ordinary temperature and at low 

 concentrations. 



It converted phenylurethane and o-tolylurethane into their mononitro 

 derivatives. 



It reacted easily with diphenylamine forming 4-nitrodiphenyl-nitrosamine, 

 and a mixture of more highly nitrated diphenyl-nitrosamines. 



2. Nitrous fumes, more especially in carbon tetrachloride solution, con- 

 verted diphenylurethane into 4-nitro- and 4'10-diuitro-diphenylurethane. 

 From phenylbenzylurethane its 4-nitro derivative was obtained. 



Nitrous fumes converted phenylbenzylether into the 4-nitro- and 4"10- 

 dinitro derivatives of the latter substance. 



R.I. A. PROC, VOL. SXXVI, SECT. B, 



[2 5] 



