The Manufacture of New Derivatives of Phenyl-amido-acetic Acid.
Year: 1890

page_text: Date of Application, 20th Mar., 1890
Complete Specification Left, 20th Dec., 1890-Accepted, 24th Jan., 1891
PROVISIONAL SPECIFICATION.
The Manufacture of New Derivatives of Phenyl-amido-acetic Acid.
I BENJAMIN WILLCOX of 47 Lincoln's Inn Fields in the County of Middlesex
Patent Agent do hereby declare the nature of this invention which has been com-
municated to me from abroad by The Farbenfabriken vormals Friedrich Bayer & Co.
of Elberfeld in the Empire of Germany to be as follows :—
By taking phenyl-amido-acetic acid such as is obtained according to Thiemann
(Ber. XIII 353) by the action of ammonia upon mandelic acid and mixing it in an
alkaline solution with the calculated quantity of benzoyl-chloride it can be converted
into a heretofore unknown derivativo namely benzoyl-phenyl-amido-acetic acid.
The process may be conducted as follows:-
15 kilos. of phenyl-amido-acetic acid are dissolved in 5 kilos. of 25 per cent. soda
lye heated to 50 degrees Centigrade and mixed with 1-6 kilos. of benzoyl-chloride
with continual agitation. The resulting solution is diluted with water filtered and
acidulated with hydrochloric acid. A syrupy mass is precipitated which quickly
solidifies.
In order to purify the product or remove any unchanged phenyl-amido-acetic acid
and any benzoic acid that is or may be formed it is treated or extracted first with
hydrochloric acid and then repeatedly boiled down with water. The mass remaining is
the new benzoyl-phenyl-amido-acetic acid and it may be purified by solution in
alcohol. It melts at 1755 degrees Centigrade and unlike phenyl-amido-acetic acid
is very difficultly soluble in water and crystallises in white needles.
By melting this combination together with phenol and gradually adding a
dehydrating agent such as phosphorus-oxy-chloride another derivative namely the
phenyl-ether of benzoyl-phenyl-amido-acetic acid is obtained. This process may bo
conducted as follows:-
12 kilos. of benzoyl-phenyl-acetic acid are melted together with 0.8 kilos. of phenol
and after being cooled to about 30 degrees Centigrade are mixed and constantly
stirred with 07 kilos. of phosphorus-oxy-chloride. The reaction which then takes
place is aided at the conclusion by the application of heat. The resulting inass forms
a yellowish thick liquid solution which being taken up in a small quantity of alcohol
and poured out onto ice separates as a yellowish white solid crystalline mass which is
recrystallised out of dilute alcohol. The phenyl-ether of benzoyl-phenyl-amido-acetic
acid (a substance whose melting point is 131 degrees Centigrade) is thus obtained in
the first place.
By concentration or mixing with alkali there is obtained from the solution a com-
pound or derivative whose melting point is 101 degrees Centigrade and which
according to analysis is to be regarded as the anhydrite of the phenyl-ether of the
benzoyl-phenyl-amido-acetic acid. This product can also be obtained by treating
the phenyl-ether of the benzoyl-phenyl-amido-acetic acid itself with phosphorus-oxy-
chloride.
Dated this 20th day of March 1890

page_text: COMPLETE SPECIFICATION.
The Manufacture of New Derivatives of Phenyl-amido-acetic Acid.
I BENJAMIN WILLCOX of 47 Lincoln's Inn Fields in the County of Middlesex
Patent Agent do hereby declare the nature of this invention (which has been com-
municated to me from abroad by Farbenfabriken vormals Friedrich Bayer & Co.
of Elberfeld in the Empire of Germany) and in what manner the same is to be
performed, to be particularly described and ascertained in and by the following
statement :-
If phenyl-amido-acetic acid such as is obtained according to Thiemann (Berichte
XIII, 353) by the action of ammonia on mandelic acid be mixed in an alkaline
solution with the calculated quantity of benzoyl-chloride it is converted into a
heretofore unknown derivative namely benzoyl-phenyl-amido-acetic acid.
The process may be conducted as follows:-
15 kilos. of phenyl-amido-acetic acid are dissolved in 5 kilos. of 25 per cent. soda
lye, heated to 50 degrees Centigrade and the solution is thoroughly mixed with
1.6 kilos. of benzoyl-chloride. The resulting solution is diluted with water, filtered
and acidulated with hydrochloric acid. A syrupy mass is precipitated which quickly
solidifies. In order to purify the product or remove any unchanged phenyl-amido-
acetic acid and any benzoic acid that is or may be formed, it is treated or extracted
first with hydrochloric acid and then repeatedly extracted with boiling water. The
remaining mass is the new benzoyl-phenyl-amido-acetic acid, and it may be purified
by crystallization from alcohol. It melts at 175.5 degrees Centigrade and is very
difficultly soluble in water and crystallises in white needles.
By melting this combination together with phenol and gradually adding to the
mixture a deliydrating agent such as for example phosphorus-oxy-chloride, another
derivative namely the phenyl-ether of benzoyl-phenyl-amido-acetic acid is obtained.
This process may be conducted as follows-1-2 kilos. of benzoyl-phenyl-acetic acid
are melted together with 0.8 kilo. of phenol and after the mixture has been cooled to
about 30 degrees Centigrade it is thoroughly mixed by constant stirring with 0-7 kilo.
of phosphorus-oxy-chloride. The reaction which then takes place is aided towards
its conclusion by the application of heat. The resulting product is a yellowish thick
liquid and if this be dissolved in a small quantity of alcohol and poured onto ice, a
yellowish white solid crystalline mass separates which may be purified by recrystalli-
sation from dilute alcohol. The phenyl-ether of benzoyl-phenyl-amido-acetic acid
(a substance whose melting point is 131 degrees Centigrade) is thus obtained in the
first place.
By concentration or mixing with alkali there is obtained from the solution a com-
pound or derivative whose melting point is 101 degrees Centigrade which according
to analysis is to be regarded as the anhydrite of the phenyl-ether of the benzoyl-
phenyl-amido-acetic acid. This product can also be obtained by treating the phenyl-
ether of benzoyl-phenyl-amido-acetic acid itself with phosphorus-oxy-chloride at
higher temperature.
Having now particularly described and ascertained the nature of the said inven-
tion and in what manner the same is to be performed, I declare that what I
claim is
I. The process for the manufacture of benzoyl-phenyl-amido-acetic acid by the
action of benzoyl-chloride upon an alkaline solution of phenyl-amido-acetic acid.
II. The process for the manufacture of the phenyl-ether of benzoyl-phenyl-amido-
acetic acid and the anhydride thereof, consisting in treating the benzoyl-phenyl-amido-
acetic acid claimed in the preceding claiming clause, with phenol and a condensing
agent such for instance as phosphorus-oxy-chloride.
III. The process for manufacturing the anhydride of the phenyl-ether, claimed in

page_text: the second claiming clause, consisting in treating the same with a condensing agent
such for instance as phosphorus-oxy-chloride at a higher temperature.
IV. The new products described.
J. H. JOHNSON & Co.,
Agents.