Ryan and Egan — Condensation of Nitrosophenylur ethane^ ^c. 831 



other than condensation, during the course of the reaction, it is probable that 

 the urethane undergoes hydrolysis to nitrosoaniline, and that the latter then 

 condenses with the amine, forming an indamine : — 



CgHjOOC NH- 



NO 



•NO 



CH, 



NH 



An indamine having this formula has already been prepared by Bernthsen 

 and Schweitzer (Liebig's Annalen, ccxxxvi, p. 343) by the oxidation of a 

 mixture of the hydrochloride of jj-phenylenediamine and m-toluylenediamine 

 by means of ferric chloride. Although the description of the dye obtained by 

 us differs slightly from that given by Bernthsen and Schweitzer for their 

 substance, it is very probable that the two substances are identical. 



EXPEEIMENTAL. 

 1. Preparation of Nitrosophenylwethane. 

 A mixture of 600 c.c. of concentrated sulphuric acid and 400 c.c. of water 

 was cooled to 30° C, and 20 g. of phenylurethane were added to it. The 

 mixture was stirred until the solid had all dissolved. The solution was then 

 cooled to - 15° C, and another solution of 8'4 g. of sodium nitrite, in 50 c.c. 

 of water, was added to it drop by drop. The deep-red solution was removed 

 from the freezing mixture and was allowed to remain for an hour at the 

 temperature of the room. The mixture was then poured into a vessel 

 containing 2 kilos of powdered ice, and the green solid which was precipitated 

 was finally filtered and washed with iced water. The product was dried in a 

 vacuum, and was fi'eed from unclianged phenylurethane by extracting the 

 latter with warm light petroleum. It was then dissolved in hot benzene, 

 from which it separated as a dark-green powder, which melted at 147° C, 

 and gave on analysis the following results : — 



01620 g. substance gave 20*2 c.c. moist N at 16° 0. and 756 m.m., 

 corresponding to N 14'46. 

 CgHioOsN, requires N 14-44. 



Nitrosopheny lure thane is almost insoluble in light petroleum, but dissolves 

 easily in alcohol, ether, chloroform, or hot benzene. 



R.l.A. PKOC, VOL. XSXVI, SKCI. B. [2 M] 



