JACKSON AND GALLIVAN. TEIBROMANILINE. 49 



acid dissolves it, and the addition of water to the solution gives a white 

 precipitate. 



When the tribromphenylurethane was boiled with aniline under a 

 reverse condenser, a substance was obtained, after removing the excess 

 of aniline with dilute hydrochloric acid, which crystallized from alcohol 

 in very long needles, melted at 235°, and contained no halogen. There 

 was no doubt, therefore, that it was diphenylurea (C6H5NH)2CO, and 

 that the aniline had replaced both the ethoxy group of the ester and the 

 tribrompheuylimido group by phenylimido radicals. 



Tribromacetanilid, CeHaBrsNHCOCHg, NH 1, Brs 3, 4, 5. 



Eight grams of the perfectly dry tribromaniline were mixed in small 

 portions at a time with a large excess of acetic anhydride, and the dark 

 colored solution warmed on the steam bath for a few minutes. The sub- 

 stance was then precipitated by pouring its solution into water, and 

 purified by many recrystallizations from alcohol, after which it was dried 

 at 100°, and analyzed with the following results: — 



I. 0.1817 gram of the substance gave 0.2756 gram of argentic bromide 



by the method of Carius. 

 II. 0.1 114 gram of the substance gave 0.1691 gram of argentic bromide. 



Bromine 



Properties. — This tribromacetanilid crystallizes from alcohol in white 

 slightly radiating brushes made up of very small needles, or in globular 

 groujjs of needles looking like chestnut burs. It melts at 253° -254°. 

 The tribromacetanilid Nil 1, Brg 2, 4, 6 melts at 232° according to 

 Remmers. Our acetanilid is soluble in benzol, and in hot alcohol, but 

 only slightly soluble in cold alcohol ; soluble with difficulty in ether or 

 chloroform ; essentially insoluble in ligroin. Sulphuric acid saponifies 

 it only after long boiling. Fuming nitric acid converts it into the uitro 

 compound described below. 



TrIBROMNITRO ACETANILID, CeHBrgNOaNHCOCHg, 



NH 1, Brg 3, 4, 5, NO. 2. 



To prepare this substance twenty grams of the dry tribromacetanilid 

 were added in small portions at a time to a quantity of nitric acid of 

 specific gravity 1.50. As the reaction is vigorous, the flask must be 



VOL. XXXIII. — 4. 



