Production of a Diamidophenolester and its Acid Derivatives.
Year: 1893

page_text: Date of Application, 1st July, 1893-Accepted, 19th Aug., 1893
COMPLETE SPECIFICATION.
Production of a Diamidophenolester and its Acid Derivatives.
We PROSPER MONNET of 8 Quai de Retz Lyons France and MAX CARL
TRAUB of 184 Grenzacher Strasse Basel Switzerland, Chemist do hereby declare
the nature of this invention and in what manner the same is to be performed, to
be particularly described and ascertained in and by the following statement :-
This invention relates to the production of a diamidophenol ester and its acid
derivatives. The ester is obtained by reduction of the corresponding dinitro-
phenolester by the known methods.
in question namely the a-diamidophenetol
The diamidophenol - ester
OC₂H (1)
CH₂ NH, (2) is in its pure condition a colourless fluid which cannot be
NH, (4)
distilled without being decomposed, which, by exposure to air, quickly becomes
changed, but, on the other hand, forms permanent salts with acids. For instance,
the hydrochlorate presents white crystals very easily soluble in water, but insoluble
or soluble with great difficulty in concentrated hydrochloric acid.
For production of a-dianidophenetol (a-diamidophenolethylether) we employ
a-dinitrophenetol as obtained by ethylising a-dinitrophenol or by treating
a-dinitrochlorbenzol with alcoholic alkali according to Willgerodt (Ber. XII. 762).
11 kilos. dinitrophenetol are dissolved in 25 kilos. warm 95 per cent. alcohol and
the solution is carefully introduced into a heated mixture of 100 kilos. of 25 per cent.
hydrochloric acid and 36 kilos. tin, so that the mixture becomes heated even to
boiling, the alcohol which is distilled off can be led through a cooler and so
recovered. When the reduction is completed, the liquid is saturated with hydro-
chloric acid gas; the double tin salt of the diamidophenetol hydrochlorate is thus
precipitated as a white crystalline mass which is separated from the mother liquor
by filtration and pressure.
By treating the aqueous solution of the double salt with sulphuretted hydrogen
the tin is eliminated, and by steaming the filtrate the diamidophenetol hydrochlorate
is obtained, which for farther purification is dissolved in water and precipitated
with hydrochloric acid gas.
The reduction can also be effected otherwise; for instance with zinc or iron with
acetic or hydrochloric acid.
For production of the free diamidophenetol the solution of either the double tin
salt or of the hydrochlorate salt of the diamidophenetol is decomposed by alkalies
or alkaline carbonates and the base is extracted with ether.
By treating the diamidophenetol with organic acids or their chlorides or
anhydrides, acid derivatives of this diamidophenolester can be produced. For
example, for production of a diacetyl derivative 4.5 kilos. of diamidophenetol
hydrochlorate is mixed with 3-5 kilos. of anhydrous sodium acetate and over the
mixture are poured 4 kilos. of anhydrous acetic acid. The acetylising then results
without application of external heat. When for the anhydrous acetic acid, glacial
acetic acid is substituted, the reaction must be started by heating.
The mixture is freed from the acetic acid and its anhydride by blowing steam
through it, it is thoroughly washed with water and the residue is crystallised out
of hot alcohol. This diacetyldiamidophenetol forms white granular crystals fusing
at 193° C., not readily soluble in cold water but easily soluble in hot water.
The acetylising can be effected with the free diamidophenetol in the same way
as with the diamidophenetol hydrochlorate, and for the acetic acid may be
1 its oblarida

page_text: The diamidophenetolester produced by the processes above set forth and its acid
derivatives can be applied to the manufacture of dye stuffs and medicines.
Having now particularly described and ascertained the nature of our said inven-
tion and in what inanner the same is to be performed we declare that what we
claim is:
1. The process for production of a diamido-phenol-ester (diamidophenetol) by
reducing the corresponding dinitrophenolester (dinitrophenetol) with suitable
reducing agents such as tin, zinc or iron with acetic or hydrochloric acid,
substantially as described.
2. The conversion of the phenetol-ester obtained as described in the first claim
into its acid derivatives by treating this ester with organic acids or their chlorides
or anhydrides, substantially as described.
3. The diamidophenetol and its diacetyl derivative produced as herein
described.
Dated this lnd th
T1000
ABEL & IMRAY,
Agents for the Applicants.