OF ARTS AND SCIENCES. 117 



On treating phenylisocyanide in chloroform solution with one 

 molecule of bromine at 0°, absorption takes place instantly with- 

 out a trace of hydrobromic acid being formed; after distilling off 

 the chloroform, a yellow oil, probably C 6 H 5 ]S"=CBr2, remains, which 

 could not be distilled in vacuum, nor be otherwise purified.* On 

 adding to a solution of phenylisocyanide in carbon bisulphide, a 

 carbon bisulphide solution of iodine (1 molecule), immediate de- 

 colorization of the iodine is noticed, as well as a marked evolution 

 of heat, and a dark yellow oil, probably the iodide, C 6 H 5 N=CI 2 , 

 obtained. 



C 6 H 5 N=C( 

 Mesoxanilid-imidechloride, CO 



C 6 H 6 N</ 



X C1 



To 5c.c. phenylisocyanide, cooled to —20°, are added 5c.c. of 

 phosgene t (cooled to —20°), and the mixture protected by calcic 

 chloride tubes from moist air. After standing for an hour at —20°, 

 the mixture is taken out of the freezing solution until the temper- 

 ature has risen to about 0°, and then cooled again, etc., until no 

 spontaneous evolution of heat is noticed. The experiment cannot 

 well be carried out with larger quantities than given above : 16 cc, 

 e. g., of a mixture in a tube cooled with ice and salt reacted all at 

 Once, while attempting to seal it up, so energetically that balf the 

 mixture was thrown out of the tube. 



Several portions treated as above mentioned were therefore united, 

 and the excess of phosgene removed by heating on a water 

 bath, and the residual oil, which contains no trace of isonitrile, 

 fractionated under diminished pressure. A viscous hygroscopic 

 j-ellow oil is obtained, having an acid and at the same time an 

 agreeable smell, which boils with slight decomposition at 145°- 

 152° at 15-20 mm. pressure. 



* Tscherniak, Bull, de la Soc. Chim., XXX. 185, obtained in a similar man- 

 ner, by treating methylisocyanide with bromine, a yellow unstable oil, which 

 could not be purified, and which he did not study further. 



t The same result is obtained on pouring the isonitrile into the phosgene. 



