CeH8.N(CHs)(CaHsO).  Methyl-acetan-

ilid.
(CeH8.N)C0,  Phenyl-cyanate.
(CeH5N)CS.  Phenyl  mustard  oil.
!•  Primary  Monamines. — ^This  most  important  class  is  formed  most
readily  by  the  reduction  of  the  corresponding  compounds  in  acid  solution,
as  already  mentioned.    This  is  the  process  used  in  the  technical  manu-


6o8  ORGANIC  CHEMISTRY.
facture  of  aniline  and  its  homologues.  If  a  dinitro  compound  is  taken
we  may  obtain  by  partial  reduction  a  nitro-amido  compound,  such  as
nitraniline.  Primary  monamines,  with  the  NH^  groups  in  the  side-
chain,  Hke  benzylamine,  are  formed  differently.  These  result  from  the
action  of  ammonia  upon  such  halogen  derivatives  as  contain  the  halogen
in  the  side-group:   C,R,,CRJC\  +  NH3  =  CgH,.CH2NH2  +  HCl.
The  determination  as  to  whether  the  amido  group  may  be  attached  to
the  nucleus  or  to  the  side-group  can  be  had  by  one  of  two  reactions:  first,
only  those  with  the  amido  group  in  the  side-chain  result  by  the. action
of  ammonia  upon  a  haloid  derivative  of  a  hydrocarbon;  second,  only
the  primary  amines  with  the  NHj  group  in  the  nucleus  are  changed  by
nitrous  acid  into  diazo  compounds,  according  to  the  reaction.
CeHsNHa.HCl     4      HNOa     :        CeHo— N     N— CI      ;      2HaO.
Aniline  Hydrochloride.  Diazo-Benzene  Chloride.
Two  Other  characteristic  and  important  reactions  for  primary  amines
may  be  mentioned.  By  the  action  of  acids  or  acid  anhydrides  upon  these
amines  the  hydrogen  of  the  NHj  group  is  replaced  by  an  acid  radical.
These  compounds  are  called  anilids:  .  ■    \     >

'  '/  CeHsNHa     +     CH3COOH     -.     CeHcNHCCHaCO)     -\-     HaO.
Aniline.  Acetic  Acid.  Acetanilid.
With  chloroform  and  alcoholic  potash  solution  the  primary  amines  of
the  benzene  series,  just  as  those  of  the  methane  series,  yield  the  fearful-
smelling  carbylamines  (isonitriles):

CeHsNHa      :       CHCI3      •       3KOH  CeHs— NC  3KCI  3H2O.
