Derivatives of Tolidin. 493 
Tetra-acetyl Tolidin. 
This is probably the most interesting of all the deriva- 
tions of Tolidin, inasmuch as it is, with one exception, the 
only example of a primary base in which both of the hydro- 
gen atoms in the amidogen group (JVH,) have been re- 
placed by the acetyl radicle. The only other compound of 
this class is Diacetanilid.* C,H, V (C,H, O),. Hoffmann 
prepared this by the action of glacial acetic acid on phenyl 
mustard oil in a sealed tube at 130°—140 C. 
C,H, NCS + 20, H, 0, =C, H, N (0, H, 0), + 00, 
+ 4, 8. 
From the readiness with which the acetyl radicle united 
with the tolidin it was supposed that a similar compound 
might be obtained directly by treating diacetyl tolidin with 
acetic anhydride. Accordingly diacetyl tolidin was, with 
6-7 times its weight of acetic anhydride sealed in tubes and 
submitted to a temperature of 180°C for six hours. The 
tubes were then found to contain ina dark fluid acicular 
erystals, which were soluble in alcohol, ether, benzol and 
and acetic acid, but insoluble in water. After purification, 
the substance was found to crystallize in long, silky, snow 
white needles, melting at 210° and on analysis gave the 
following results :— 
Calcnlated for C,, H,, N, O, 
Theory. Found. 
ie 10h 
C == 69.47 69.28 eres 
i 6.32 6.61 seee 
N= 7.37 fee 7.65 
O = 16.84 aelle disiee 
When treated with dilute alkalies it at once broke down 
into diacetyl tolidin and acetic acid. The two acetyl deriva- 
tions of Tolidin may be thus represented :— 
CH, CH, 
l {G H, O l C, H, O 
C, H,—-Ni C,; H,—-N1 C, H, O 
{ez { H, O 
’. H,—N1 C, H, O C, Hy,—-N1C, H; 0 
CH, CH, 
Diacery1-ToLimim. Tprra-AcpryL TOLIDIN, 
