114 PROCEEDINGS OP THE AMERICAN ACADEMY 



condenser, reduction of the mercuric oxide is noticed at 40°, and 

 also the characteristic smell of phenylcyanate ohserved. The 

 quantity of this substance formed was very small, and a large 

 amount of gaseous products appear, so that it would necessitate 

 the sacrifice of too much material in order to obtain sufficient phe- 

 nylcyanate for an analysis. The experiments were therefore not 

 continued, especially as Gautier* has already accomplished this in 

 the case of methylisocyanide. 



Isocyanphenylchloride, or Phenylimidocarbonylchloride, 



C 6 H 5 N = OCl 2 . 



On passing dry chlorine iuto a well cooled solution of phenyliso- 

 cyanide in five to six times its volume of chloroform, the gas is 

 absorbed instantly and completely, without the slightest trace of 

 hydrochloric acid being formed. The reaction is complete when 

 the color of the solution changes suddenly from blue to yellow. 

 The chloroform solution is washed immediately with dilute sodic 

 hydrate, dried with calcic chloride, and then fractionated. A 

 colorless oil is obtained boiling at 204°-205° (uncorr.), or at 209°- 

 210° (thermometer entirely in the vapor). 



0.2740 gram substance gave 0.4822 gram C0 2 and 0.0755 gram 



H 2 0. 

 0.0779 gram substance gave 0.1298 gram AgCl on ignition with 



CaO. 



Theory for C 7 H 5 NC1 2 . Found. 



C 48.27 47.99 



H 2.88 3.06 



CI 40.80 41.22 



Isocyanphenylchloride is a colorless, sharp-smelling oil, which 

 attacks the eyes strongly. On heating it with acetic acid, acet- 

 anilide is formed; with water, s. diphenylurea; with silver oxide, 

 phenylcyanate; with alcohol, phenylurethane. On heating it with 

 aniline, all at once a very violent reaction takes place, which can 

 only be regulated by taking small quantities (about 2 grams). 

 There is left a white mass, the hydrochloride of a base, which 

 crystallizes from dilute alcohol in colorless scales, melting at 241°. 

 On addition of ammonia to an aqueous solution of the salt, the free 

 base separates out. After being twice recrystallized from alcohol, 



* Loc. cit., XVII. 229. 



