Improvements relating to the Production of Acetyl and Propionyl Compounds of P-oxyphenylurethanes or their Ethers
Year: 1892

page_text: Date of Application, 10th Dec., 1892
Complete Specification Left, 9th Sept., 1893-Accepted, 11th Nov., 1893
Improvements relating to the Production of Acetyl and Propionyl
Compounds of P-oxyphenylurethanes or their Ethers.
I, Professor Dr. JOSEPH FRIEDRICH FREIHERR VON MERING, of Halle on
the Saale, in the Empire of Germany, do hereby declare the nature of this invention
to be as follows:-
This invention relates to the production of acetyl or propionyl compounds of
p-oxyphenylurethanes [CH(OH)NHCOOR] and of their ethers [CH (OR¹)
NHCOOR] which have a powerful antypyretic and analgetic action R and R' in
these formulæ signifying any desired alcohol radicals. The acetyl compounds are
represented by the formula:

page_text: The manner in which the acetylization is effected may be explained by the
following examples.
PRODUCTION OF ACETYL COMPOUNDS OF P-OXYPHENYLURETHANES.
Example. The production of p-oxyphenylacetylethylurethane. For this purpose
1 heat in a vessel 10 kilogrammes of p-oxyphenylethylurethane with an equal
quantity of acetic anhydride under pressure or with a return flow for about one hour,
whereupon the excess of acetic anhydride is distilled and the residue allowed to
crystallize.
PRODUCTION OF ACETYL COMPOUNDS OF THE ETHERS OF P-OXYPHENYL-
URETHANES.
•
I heat
Example. The production of p-methoxyphenylacetylethylurethane.
10 kilogrammes of p-methoxyphenylethylurethane with an equal quantity of acetic
anhydride for about one hour in a vessel under pressure or with a return flow.
After the excess of acetic anhydride has then been distilled the residue is allowed.
to crystallize. For producing acetyl compounds of other p-oxyphenylurethanes or
their ethers I replace the said urethanes in the above examples by the corresponding
other p-oxyphenylurethanes or their ethers.
The acetic anhydride may also be replaced by another acetylizing agent, as
above stated.
When in lieu of the said acetylizing agents use is made of the corresponding
propionyl compounds, such as propionic acid propionic anhydride, propionyl
chloride. I obtain the corresponding propionyl compounds of p-oxyphenylurethanes
or their ethers.
Thus I may heat for instance 10 kilogrammes of p-oxyphenylmethylurethane
with an equal quantity of propionic anhydride in a vessel under pressure or with a
return flow. After separating the excess of propionic anhydride I allow the
product of reaction to crystallize. The compounds obtained in the described
manner are distinctly characterized, well crystallizing substances which dissolve
with difficulty or with great difficulty in cold water and easily in alcohol and radical
vinegar, and possess strongly antipyretic and analgetic properties, as 0.5 grammes 3
have been sufficient to reduce the temperature of fever by from three to four
degrees centigrade. They are chiefly designed for medicinal purposes.
According to my improved method the following compounds are produced
amongst others

page_text: hour, whereupon the excess of acetic anhydride is distilled and the residue allowed
to crystallize.
PRODUCTION OF ACETYL COMPOUNDS OF THE ETHERS OF P-OXYPHENYL-
URETHANES.
Example: The production of p-methoxyphenylacetylethylurethane. I heat
10-kilogrammes of p-methoxyphenylethylurethane with an equal quantity of acetic
anhydride for about one hour in a vessel under pressure or with a return flow.
After the excess of acetic anhydride has then been distilled the residue is allowed
to crystallize. For producing acetyl compounds of other p-oxyphenylurethanes or
their ethers, I replace the said urethanes in the above examples by the corresponding
other p-oxyphenylurethanes or their ethers.
The acetic anhydride may also be replaced by another acetylizing agent, as
above stated.
When in lieu of the said acetylizing agents use is made of the corresponding
propionyl compounds, such as propionic acid, propionic anhydride, propionyl
chloride, I obtain the corresponding propionyl compounds of p-oxyphenylurethanes
or.their ethers.
Thus I may heat for instance 10 kilogrammes of p-oxyphenylmethylurethane
with an equal quantity of propionic anhydride in a vessel under pressure or with a
return flow. After separating the excess of propionic anhydride I allow the
product of reaction to crystallize. The compounds obtained in the described
manner are distinctly characterized, well crystallizing substances which dissolve
with difficulty or with great difficulty in cold water and easily in alcohol and radical
vinegar, and possess strong antipyretic and analgetic properties, as 0.5 grammes
have been sufficient to reduce the temperature of fever by from three to
four degrees centigrade. They are chiefly designed for medicinal purposes.
According to my improved method the following compounds are produced
amongst others :-
COCH,

page_text: and easily in alcohol and radical vinegar, possess strongly antipyretic and analgetic
properties, R and R' in the above formulæ signifying alcohol radicals.
Dated this 8th day of September 1893.
HASELTINE, LAKE & Co.,
45, Southampton Buildings, London, W.C., Agents for the Applicant.