A Manual of the Chemistry of the Carbon Compounds

324 THE CHEMISTRY OF
cyanvuic acid when phenyl-urea is heated, and it is also obtained by
the action of carbonyl chloride on. aniline, and by heating aniline
with urea;—
2CA.NH, + CO { ggj = CO { Jg;%g< + 2NH8
It crystallizes in silky white needles; is insoluble in water and
volatilizes on heating.
( NHfC H ^
Ethyl carbanilate ov pfonyl-uretkanc CO •] Q^, W° ''is found when
aniline is acted upon by chlorocarbonic ether (p_age 118). It forms
large crystals, and boils at 237°. By heating it with phosphorus
pentoxide, it is resolved into ethyl alcohol and cwlanil or phenyl
carbimidc O j- N, a very refractive liquid, boiling at 163°, and
possessing a most pungent smell.
When this body is brought in contact with a little triethylphosphine,
it is converted into the polymeric diphenyl dicarUmide
(phenyl dicyanate)' feffi J- Na, forming large beautiful crystals,
melting at 175°. At a high temperature it is resolved again into
two molecules of carbaniL It combines with alcohol, forming ethyl
dipIunylalhphoM.dc C6H6.N I COOC^H"^} (8ee pa 8 e 120 >' crystal "
lizing in fine needles, melting at 98°.
IMphocarbanUide OS j jutr rlir * 8 produced by boiling an alcoholic
solution of aniline and carbon disulphide as long as hydrogen sulphide
is given off. It forms iridescent plates, which are sparingly soluble
in water, more freely in alcohol, and have a bitter taste,
CHI
Pkenukulpkocarbimide or Phmyl mustard*oil a r« f N,—To prepare
this compound, sulphooatbanilide is heated with fuming hydrochloric
acid. It is a colourless liquid, boiling at 222°, and smelling
like cemmon mustard-oil.
Omnilide (CgH^jN^H^CjOA is obtained, together with formanilide,
when aniline oxalate is heated. It is insoluble in water, and sublimes
on heating in shining crystals, melting at 245", By heating
aniline with an excess of oxalic acid, the monobasic oxanilic add
£ IT
C| Q Q Qjr is formed, which is soluble in water,
C'yananilide C0H6N \ Q« is formed by passing cyanogen chloride
into a solution of aniline in ether. It is an amorphous mass,
MelanUim or dvphenylrffiumi&ine C(NH)(NH,C0H5)a is a weak
base, forming crystalline salts, and is produced by passing cyanogen
chloride into pure aniline. An isomeric compound is formed when
guanidiue hydrochloride is gently heated with aniline. The isotnerism