The Manufacture or Production of Para-phenetidin-succinic Acid, and of Para-phenetidin-dioxy-succinic Acid.
Year: 1895

page_text: Date of Application, 27th July, 1895-Accepted, 12th Oct.,
1895
CUMI DEIN DI LUIFICATION.
The Manufacture or Production of Para-phenetidin-succinic Acid,
and of Para-phenetidin-dioxy-succinic Acid.
I GEORGE WILLIAM JOHNSON of 47 Lincoln's Inn Fields in the County of
London Patent Agent, do hereby declare the nature of this invention (which has
been communicated to me from abroad by Dr. F. von Heyden Nachfolger of
Radebeul near Dresden in the German Empire) to be as follows:-
Succinic acid and dioxy-succinic acid (tartaric acid) are in the presence of
para-phenetidin (para-amido-phenetol) capable of forming a variety of compounds
which are of the nature of anilides, and of which those in which the free carbon
acid groups are still present, yield extremely useful medicinal substances owing to
their great solubility in water and also owing to their property of forming very
readily soluble salts.
These new substances, prepared by the improved process forming the subject
of this invention may be described as follows and expressed by the following
formulæ.
The following is an example of the course to be adopted in preparing these new
substances.
A mixture of one molecular proportion or rather more, of the acid to be dealt
with and of one molecular proportion of para-phenetidin is heated for a number of
hours to a temperature of about 150° Centigrade. An example of a suitable
mixture is 55 parts by weight of tartaric acid or 45 parts by weight of succinic
acid and 41 parts by weight of para phenetidin.
The product of the reaction is boiled with a soda solution. From the solution
obtained and by the addition thereto of suitable mineral acids there is precipitated
either phenetidin-tartaric acid or phenetidin succinic acid. The product is purified
by crystallization, i.e. separated from the water. Each of the substances dissolves
comparatively readily in cold water, and with great readiness in hot water and in
soda solution. The phenetidin-tartaric acid forms small plates or scales the point
of fusion of which is 195° Centigrade 4095 grammes, require for neutralization
14.9 cubic centimetres of tenth normal soda solution instead of 15.2 cubic centi-
metres for

page_text: The phenetidin-succinic acid forms scales the melting point of which is from
163 to 164° Centigrade.
3385 grammes require for neutralization 14.8 cubic centimetres of tenth normal
soda solution 14.3 cubic centimetres will be required for the formula:
CHOH)(CONHCHOC₂H¸) 20
A liberal yield of these diphenetide substances will be obtained by including in
the above recipe two molecular proportions of phenetidin and they will melt at
156° Centigrade and 265° Centigrade, respectively, are but with great difficulty
soluble in water and are insoluble in soda solution and offer no advantages for
pharmaceutical or medicinal purposes over other agents belonging to the same
group or series.
By being melted with succinic acid or tartaric acid, they are converted into
phenetidin-succinic acid or phenetidin-tartaric acid respectively.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed I declare that what
I claim is
The manufacture or production of para-phenetidin succinic acid and para-
phenetidin-dioxy-succinic acid by heating a mixture of one molecular proportion of
phenetidin with one molecular proportion, or more than one molecular proportion of
succinic acid or tartaric acid respectively.
Dated this 27th day of July 1895.
JOHNSONS & WILLCOX,
47 Lincoln's Inn Fields, London, W.C., Agents.