4-NITRO-5-METHYL-2-SULPHOBENZOIC ACID 197 
were very fine. The melting point seemed to be at 342° ; but 
fusion did not occur until after the product was quite black 
with heating. This behavior corresponds with that of the sym- 
metrical anilides which have been described by others. The 
formula is given from the fact that it is formed only by the 
action of the unsymmetrical acid chloride, and also that the 
two anilido groups are intact in the compound.^® 
The unsymmetrical anilide is insoluble in most ordinary sol- 
vents and this is a general characteristic of such substances. Car- 
bon tetrachloride, alcohol and benzene have little if any action 
on it. Analysis for sulphur was by Liebig’s method and that 
for nitrogen by the modified Gunning method. 
.1962 grams substance required 19.49 cc .1088N HCl. 
.2187 grams substance gave .1237 grams barium sulphate. 
.2253 grams substance gave .1261 grams barium sulphate. 
Theory for C 10 H 1 TO 5 N 3 S Found 
Nitrogen, 10.22 per cent. 10.02 per cent. 
Sulphur, 7.78 per cent. 7.77- 7.69 per cent. 
The third substance produced by the action of aniline on the 
unsymmetrical acid chloride is soluble in water, and was re- 
covered by evaporating the filtrates from the various washings 
of the original dianilides. It crystallizes in clumps of needles 
whose fineness or coarseness is dependent on the rate of forma- 
tion. 
It is suspected that this body is the anilido acid, but it is not 
easy to purify and no very satisfactory analyses were obtained. 
It gives an acidity approaching that expected, but rather less, 
while it is high in nitrogen. 
The total yields of the two anilides were almost equal, but 
the weight of the third body was less than either. This latter 
fact may be due to incomplete recovery, as the substance crys- 
tallized out in a fashion which showed it to have a solubility only 
slightly less than the sodium chloride with which it was mixed. 
It is also probable that there was considerable hydrolysis to the 
4-nitro-5-methyl-2-sulphobenzoic acid. The total yield from a 
given amount of the acid chloride is not sufficient to account for 
all the material. 
TRANSFORMATIONS OF THE ANILINE DERIVATIVES. 
When either the symmetrical or unsymmetrical anilide is 
treated with phosphorous oxychloride, at boiling temperature, 
isRemsen and Hunter; Am. Chem. J., 18, 812, 1896. 
