Manufacture of New Carbonic Esters of Acidyl Derivatives of Amido Phenols, and of their Alkylised Derivatives.
Year: 1894

page_text: Date of Application, 21st Dec., 1894
Complete Specification Left, 23rd Sept., 1895-Accepted, 26th Oct., 1895
[Communicated from abroad by THE FARDWERKE, vormals MEISTER LUCIUS
AND BRUNING, of Hoechst a/Main, in the Empire of Germany, Chemical
Manufacturers.]
Manufacture of New Carbonic Esters of Acidyl Derivatives of Amido
Phenols, and of their Alkylised Derivatives.
1, OLIVER IMRAY, 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 acidyl derivatives of para-amidophenols
and their derivatives in which the nitrogen atom is alkylised in the form of their
salts, may be converted into acy lamido phenol carbonic esters or acylalkylamido-
phenol carbonic esters of the general formulæ :
Acetylethylamidophenyl-ethyl-carbonate, melting point
-methyl-
My correspondents have prepared the following new compounds by means of the
bove method.
"
95-96° C
83-84°
"
"
"
"
Acetylmethylamidophenyl-ethyl-
103-104°
"
"
"
"
.
-methyl-
145-146°
"
"
"
"
Acetylamidophenyl-ethyl-
121°
"
39
"
"
"
"
"
-methyl
-Isobutyl
-isoamyl
115-116°
33
"
"
"
116-117°
"
"
"
"
112-113°
"
"
"
"
101-102°
"
"
"
رو
"
-methyl
87-88°
"
"
"
"
84-85°
"
"
">
"
"
-methyl
104-105°
"
"
"
"
Lactylamidophenyl-ethyl
Formylamidophenyl-ethyl
The following example serves to illustrate the above method.
1.89 kilos. of acetylethylamidophenol are dissolved in the calculated quantity of
oda lyc and the solution treated with a slight excess of about 11 kilos. ethyl-
chlorcarbonate and shaken until the reaction is finished, precautions being taken to
prevent any considerable rise of temperature.
The precipitate of acetylethyl-para-amido phenylethyl carbonate thus formed is
crystallised from dilute alcohol.
The acidyl derivatives of amidophenylcarbonic esters are colourloss compounds
which crystallise well, are with difficulty soluble in cold water, easily soluble in
alcohol and hot water, less soluble in benzene and ether. They are decomposed
by beating with acids of alkalies.
.
Dated this 21st day of December 1894.
ABEL & IMRAY,
Agents for the Applicant.

page_text: Manufacture of New Carbonio Esters of Aoidyl Derivatives of Amido
Phenols, and of their Alkylised Derivatives.
I, OLIVER IMRAY, 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 base discovered that acidyl derivatives of para-amidophenols
and their derivatives in which the nitrogen atom is alkylised in the form of their
salts, may be converted into acidyl amido phenol carbonic esters or acıdyl alkyl-
amidophenol carbonic esters of the general formule.
My correspondents have prepared the following new compounds by means of the 1
above method.
Acetylethylamidophenyl-ethyl carbonate, melting point
"
-methyl-
"
Acetylmethylamidophenyl-othyl-
",
"
95-96° C.
83-84°
103-104°
"
"
"
"
"
-methyl-
145-146°
"
"
"
"
Acetylamidophenyl-ethyl-
121°
"
"
"3
331
50.
-methyl-
115-116°
"
"
"
"
19
-isobutyl-
126-1170
"
"
"
"
"
-isoumyl-
112-113°
>"
1
"
"
Lactylamidophenyl-ethyl-
101-102°
2
"
"
3.
"1.
-methyl-
87-88°
"
39+
"
"
84-85°
"
"
"
"
-methyl-
104-105°
$3
+
"
"
Formylamidophenyl-ethyl-
The following example serves to illustrate the above method.
1.89 kilos. of acetylethylamidophenol are dissolved in the calculated quantity of 2
Boda lye and the solution ticated with a slight excess, of about 11 kilos. ethyl-
chlorcarbonate and shaken until the reaction is finished, precautions being taken to
prevent any considerable rise of temperature.
The precipitate of acetylethyl-para-amido phenyl ethyl carbonate this formedus
crystallised from dilute alcohol.
The acidyl derivatives of amidophenylcarbonic esters are colourless compounds
which crystallise well, are with difficulty soluble in cold water, easily soluble,in.
alcohol and hot water, less soluble in benzene and ether. They are decomposed
by heating with acids or alkalies.
Having now particularly described and ascertained the nature of this inven-
tion and in what mauner the same is to be performed, I declare that what I'
claim 18:-
1. The herein described manufacture of carbonio esters of aris.l-amidophenol,
and of their alkyl derivatives by treating acidylamidophenols and their derivatives
of which the nitrogen atom is alkylated in the form of their salts with esters of
chlorcarbonic acid.
2

page_text: 2. The carbonic esters of acidyl amidophenol, possessing the general formulæ
NHA
NT111 An