Manufacture of Derivatives of Amido-crotonic Acid.
Year: 1892

page_text: Date of Application, 24th Mar., 1892
Complete Specification Left. 23rd Dec., 1892-Accepted, 11th Feb., 1893
PROVISIONAL SPECIFICATION.
[Communicated from abroad by the firm of C. F. BOEHRINGER J. SÖHNE, of
Waldhof, near Mannheim, Germany, Manufacturers.]
Manufacture of Derivatives of Amido-crotonic Acid.
I, CHARLES DENTON ABEL, of No. 28 Southampton Buildings, Chancery
Lane, in the County of London, Chartered Patent Agent, do hereby declare the
nature of this invention to be as follows
--
My correspondents have discovered that some derivatives of amido-crotonic acid
have remarkable therapeutic properties.
In the following I will give the description of the production of such a derivative,
namely acetylamidocrotonylanilide.
EXAMPLE.
If acetylaceticanilide either pure or in solution be brought together with aqueous
or alcoholic ammonia in slight excess, and this mixture be allowed to stand at
ordinary temperature, there will be effected in the course of 24 to 30 hours a
conversion under exclusion of water and combination of NH, with the
acetylaceticanilide.
i
С₁H„NO₂ + NH¸ = C₁H₁ (NH₂) NO + HO.
10
The product thus obtained is amidocrotonylanilide, which in most solvents is
moderately soluble in the cold, and which can be obtained pure by once
recrystallising out of alcohol.
It crystallises in colourless needles of the melting point of 146° to 147° C.
For producing acetylamidocrotonylanilide, amidocrotonylanilide is boiled with
1-12 times the quantity of acetic anhydride in connection with a reflux cooler..
The reaction liquid is mixed with water after cooling, and is separated from
the greater part of the acetic acid.
The acetyl derivative is separated as oil from the aqueous solution by means of
potash, and on being taken up by ether will readily crystallise after the evaporation
of the solvent.
It forms colourless crystals and melts at 98° C.
It is very soluble--in-water, alcohol and chloroform, and is easily soluble in hot
benzole and toluol.
Dated this 24th day of March 1892.
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
Manufacture of Derivatives of Amido-crotonic Acid.
I, CHARLES DENTON ABEL, of No. 28, Southampton Buildings, Chancery
Lane, in the County of London, Chartered Patent Agent, 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:-
My correspondents have discovered that some derivatives of amido-crotonic acid
have remarkable therapeutic properties.
In the following I will give the description of the production of such a derivative,
namely acetylamidocrotonylanilide.

page_text: EXAMPLE.
If acetylaceticanilide either pure or in solution be brought together with aqueous
or alcoholic ammonia in slight excess, and this mixture be allowed to stand at
.ordinary temperature, there will be effected in the course of 24 to 30 hours a
conversion under exclusion of water and combination of NH, with the
acetylaceticanilide,
+
CH₁NO, NH, C₁,H1, (NH2) NO + H₂O.
11
2
=
=
10
The product thus obtained is amidocrotonylanilide, which in most solvents is
moderately soluble in the cold, and which can be obtained pure by once
recrystallising out of alcohol.
It crystallises in colourless needles of the melting point of 146° to 147° C.
For producing acetylamidocrotonylanilide, amidocrotonylanilide is boiled with
1.12 times the quantity of acetic anhydride in connection with a reflux cooler.
The reaction liquid is mixed with water after cooling, and is separated from the
greater part of the acetic acid.
The acetyl derivative is separated as oil from the aqueous solution by means of
potash, and on being taken up by ether will readily crystallise after the evaporation
of the solvent.
It forms colourless crystals and melts at 98° C.
It is very soluble in water, alcohol and chloroform, and is easily soluble in hot
benzole and toluol.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, I declare that what I
claim is :-
1. A process for the preparation of amidocrotonylanilide consisting in causing
acetylaceticanilide, either alone or in solution to react upon an aqueous or alcoholic
solution of NH, substantially as described.
2. A process for the production of acetylamidocrotonylanilide consisting in
heating the amidocrotonylanilide produced as set forth in the preceding claim, for
a short time with aceticanhydride, substantially as described.
Dated this 23rd day of December 1892.
ABEL & IMRAY,
Agents for the Applicant.