4-NITRO-5-METHYL-2-SULPHOBENZOIC ACID 
199 
S0,C1 
+ 2 NHaCeHj 
C^NCeHs C^NCeHs 
CsH./^NH, CeH,/ ^NCeHs 
so, • NHCeHs so, 
Also Anscliultz and Beavis^^ give a reaction of this kind for 
maleic dianil, which they form by the action of dichlor maleic 
anil on aniline. 
ClC-C=Cl2 CIC— C=NC6H5 
li ^NCsHs + H,NC.H, ^ II Vno^Hs 
CIO— 0=0 010—0=0 
The dianil recrystallizes nicely from acetone diluted with 
water, and forms short, bright yellow, hexagonal needles. It is 
soluble in other solvents, such as benzene and alcohol, and may 
be recrystallized from them if desired. The substance when 
recrystallized melts constantly at 188°. It was analyzed for 
nitrogen and sulphur. 
.1793 g. substance requires 12.67 cc .1088N HCl. 
.1950 g. substance gives .1150 g. barium sulphate. 
Theory for C 20 H 15 O 4 N 3 S Pound 
Nitrogen, 10.69 per cent. 10.76 per cent. 
Sulphur, 8.14 per cent. 8.10 per cent. 
The anilides may be transformed into one another by various 
reagents. These processes have been worked out for various 
acids. Blanchard^^ worked with the anilides of p-brom sulpho- 
benzoic acid, Henderson^^ and others with the corresponding 
p-nitro and unsubstituted bodies. The results in every case are 
similar to those given by the anilides herein described. 
As has been stated, if either the unsymmetrical or symmetrical 
anilides are treated with phosphorous oxychloride we obtain the 
dianil. If the dianil is boiled with concentrated hydrochloric 
acid, it goes over into the colorless anil without dissolving, and 
the yellow color slowly disappears during the process. The 
melting point of the colorless solid, 202°, shows it to be the anil. 
If the dianil is boiled for some time with glacial acetic acid 
until the solution, which is vivid yellow at first, becomes colorless, 
and the solution is allowed to stand, the unsymmetrical anilide 
crystallizes out. When washed with water and dried it has a 
melting point of approximately 342°, as described previously. 
If the anil is warmed with aniline for some hours, and the 
excess of aniline distilled off with steam, the residue, when re- 
crystallized from alcohol, proves to be the fusible or symmetrical 
anilide with a melting point of 195°. 
22Eer., 28, 58, 1895. 
”Am. Chem. J., 30, 485, 1903. 
2^Am. Chem. J., 25, 1, 1901. 
