136 Scientific Proceedings, Royal Dublin Society. 



(b) In carbon tetracMoricU. — To a solution of 5 grams of plienyl-benzyliu-ethane 

 ill 50 grams of carbon tetrachloride was added a quantity of fuming nitric acid 

 (sp. g. 1'52) corresponding to four molecular amounts of the acid. 



After a few days crystals separated from the two-layered liquid formed, and on 

 removal were identified as oxalic acid, melting at 99'- 101° C. The remainder was 

 shaken for a week and allowed to stand for two months, when it was freed from 

 carbon tetrachloride by distillation under reduced pressure. 'J'he yellow oil 

 obtained became largely crystalline on standing for three weeks, giving a good 

 yield of 4-nitro-phenyl-benzylurethane, 



C.-ACTION OF NITRIC ACID ON NITRO-PHENYL-UENZYLURETHANE. 



I . — 4:-Niiro-2jJiciii/l-l>enzi/lurcf}ianc. 



One gram of 4-nilro-phenyl-benzylurethane was added slowly to 4e.c. of fuming 

 nitric acid (sp. g. 1'5;, which was kept at 0°C. during the addition of theurethane. 

 The oil which was precipitated on diluting the mixture with water was dissolved 

 in hot alcohol, from which the rhombic prisms of the triniti'O-phenyl-benzyl- 

 urethane, melting at 108°-110° C, separated. 



II. — Trinitro-phcni/l-hcnzi/lur ethane. 



To an ice-cold mixture of 2 c.c. of fuming nitric acid (sp. g. 1"52) and 2 c.c. of 

 fuming sulphuric acid (20 p c, SO3) 0'4 gram of trinitro-phenyl-benzylurethane 

 was added slowly, keeping the temperature of the mixture low. The flask was 

 then removed from the ice-cold water and allowed to remain overnight at the 

 temperature of the room. The product was precipitated by diluting the mixture 

 with water, and was then recrystallised from alcohol. It proved to be the tetranitro- 

 phenyl-benzylurethane already described, in a slightly impure condition (melting 

 at 123°-125°C.). 



D.— PREPARATION OF Id-NITRO-PHENYL-BENZYLURETHANE. 



10-Nitro-phenyl-benzylurethane, which was prepared from 4-nitro-benzyl- 

 chloride and aniline by the method of Paal and Sprenger [Ber. d. Dtsch. Chem. 

 Ges., XXX (1897), p. 69], v/as heated with a benzene solution of ethyl ehloroformate 

 for six hours under a reflux condenser. The greenish-yellow oil left after 

 distillation of the benzene was dissolved in hot alcohol, from wliich a somewhat 

 oily crystalline solid separated on standing. After several recrystallisations the 

 substance was obtained in the form of almost colourless rhombic plates, which 

 melted at 68^-69°C., were identical neither with the original amine nor with the 

 4-nitro-phenyl-benzylnrethane described above, and gave on analysis the following 

 results : — 



0T642 g. of the substance gave 13'8 c.c. of moist nitrogen at 13° C. and 755 mm., 



corresponding to N 9 87. 

 CisHisOiNs requires N 9-3b. 



VQ-Nitro-2Jhen]il-hensi/htrcthanc is soluble in warm petroleum, ether, or alcohol, 

 and is readily soluble in ether, chloroform, or carbon tetrachloride. 



