1S6 
IOWA ACADEMY OF SCIENCE 
tate, which was. insoluble in water was now treated with dilute 
sodium hydroxide in which it was almost completely soluble. 
Only a faint cloudiness remained in the solutioUj hence the 
conclusion was that nothing but the merest traces of anil could 
have been formed. The amount of anil produced from five 
grams of pure unsymmetrical acid chloride was only great 
enough to stain the filter paper. No positive identification of 
it was possible. This corresponds with the observation by 
Holmes^^ that no anil was produced from the unsymmetrical 
chloride of o-sulphobenzoic acid. From this solution the anilide 
was precipitated b^ hydrochloric acid as in the case of the 
symmetrical compound, washed, dried and recrystallized from 
alcohol. It was found in this case, however, that a large por- 
tion of the. precipitated material would not dissolve even in hot 
alcohol. This substance, which proved to be the unsymmetrical 
anilide, will be described later. 
Symmetrical Anilide. 
The alcohol solution mentioned above, on cooling gave a mass 
of soft needles which on recrystallization melted at 195°. This 
substance is identical with the anilide formed from the sym- 
metrical chloride, and in conformity with the argument used 
in that case, is known as the symmetrical anilide. It is taste- 
less. The anilide was analyzed for sulphur by Pringsheim’s 
method, and for nitrogen by the modified Grunning method. 
.1461 g. substance required 9.78 cc .1084N HCl. 
.1661 g. substance required 11.00 cc .1084N HCl. 
.1775 g. substance gave .0255 X 4 g. barium sulphate. 
Theory for C 20 H 17 O 5 N 3 S Pound 
Nitrogen, 10.22 per cent. 10.15-10.06 per cent. 
Sulphur, 7.78 per cent. 7.91 per cent. 
The Unsymmetrical Anilide. 
NO, • CHs 
C=(NHOeH5). 
SO, 
( 1 ) 
(a) 
The substance insoluble in alcohol was purified by dissolving 
in hot 75 per cent alcohol with the aid of sodium hydroxide 
added drop by drop until the precipitate had disappeared. To 
this solution acid was added, and the precipitate which formed 
after a delay of some seconds was nicely crystalline. The crystals 
I'Am. Chem. J., 30, 275, 1903. 
