A New Process for Manufacturing Compounds of Acetamide.
Year: 1898

page_text: Date of Application, 6th June, 1898
Complete Specification Left, 27th Feb., 1899-Accepted, 1st Apr., 1899
[Communicated from abroad by THE ACTIEN GESELLSCHAFT FÜR ANILIN FABRIKATION
of Berlin, in the Empire of Germany, Chemical Manufacturers.]
A New Process for Manufacturing Compounds of Acetamide.
f
I, CHARLES DENTON ABEL, of Birkbeck Bank Chambers, Southampton Buildings,.
Chancery Lane, in the County of London, Consulting Engineer and Chartered Patent-
Agent, do hereby declare the nature of this invention to be as follows:-
My foreign correspondents have discovered a new process for the manufacture of
acetamide derivatives which may be used for medicinal purposes.
This process is effected by allowing chloracetamide to react upon alkalı salts of
phenols, substituted phenols or carboxylic acids of the aromatic series.
Some of these compounds have already been prepared by other processes, but as -
these are rather troublesome the new process is of high technical value.
The action of chloracetamide upon the above named alkalı salts is represented by
the following general formulae:
X representing an aromatic nucleus and M an alkali metal.
According to the researches of my foreign correspondents good results are obtained
with this process if phenols such as phenol, a-naphthol, B-naphthol &c., substituted
phenols, such as guajacol, nitrophenol, acetyl-p-amidophenol, laotyl-p-amido-
phenol &e, or carboxylic acids, or their substitution products, such as benzoic acid, -
nitrobenzoic acids, salicylic acid &c be used.
A New Process for Manufacturing Compounds of Acetamide.
T
I, CHARLES DENTON ABEL, of Birkbeck Bank Chambers, Southampton Buildings,
Chancery Lane, in the County of London, Consulting Engineer and Chartered Patent
Agent, do hereby declare the nature of this invention (as communicated to me from
abroad by The Actien Gesellschaft fur Anilin Fabrikation, of Berlin, in the Empire of..
Germany, Chemical Manufacturers,) and in what manner the same is to be
[Price 8d.l

page_text: performed, to be particularly described and ascertained in and by the following
statement :-
My foreign correspondents have discovered a new process for the manufacture of
acetamide derivatives which may be used for medicinal purposes.
This process is effected by allowing chlor-acetamide to react upon alkalı salts of 5
phenols, substituted phenols or carboxylic acids of the aromatic series.
Some of these compounds have already been prepared by other processes,
these are rather troublesome the new process is of high technical value.
but as
The action of chloracetamide upon the above named alkalı salts is represented by
the following general equations;
1

page_text: then with water and finally recrystallized from alcohol. The para-nitrophenoxyl-
acetamide thus obtained forms colourless prisms or needles which melt at 154-156° C.
(4)
If in the preceding example 13.7 kilos. salicylamide or 33.1 kilos. tribromphenol are
substituted for para-nitrophenol, otherwise proceeding in the manner above indicated.
the following derivatives are respectively obtained: acetamide ether of salicylamide
(1) (2)
CH, (CONH) OCH, CONH, which forms colourless needles without taste or sinell,
has a melting point of 208-210° C and is hardly soluble in cold water but readily
soluble in boiling water; tribromophenoxylacetamide CH₂ (Br). OCH, CONH₂
which forms colourless crystals having a bitter taste, melts at 200° C and is hardly
soluble in cold water or alcohol but more readily soluble in boiling alcohol.

page_text: about 140° C. The mixture at first melts, but becomes solid after several hours
heating. It is then recrystallized from boiling water or alcohol as above described.
EXAMPLE IX.
27.6 kilos. of para-oxybenzoic acid are dissolved in 35 kilos. of potash lye containing
32 per cent. of KOH, and 35 kilos. of alcohol The solution 18 heated with 18 kilos.
of chloracetamide on the water bath in a vessel provided with a reflux-condenser.
After boiling for about 8 hours the mixture is thrown into 350 litres of water, the
solution 18 made alkaline by addition of sodium carbonate, the separated crystals are
filtered, washed with water and recrystallized from boiling water. The substance thus
obtained is the acetamide ether of paraoxybenzoic acid. It forms colourless crystals
melting at 260° C.
EXAMPLE X.
33-4 kilos, orthonitrobenzoic acid are dissolved in 35 kilos. of potash lye containing
32 per cent KOH, and 110 kilos. alcohol and the mixture heated for 13 hours with
18 kilos. of chloracetamide on the water bath The larger part of the alcohol is then
distilled off, the product for med 18 precipitated by addition of water, the mixture is
made alkaline by means of sodium carbonate, and the separated crystals are filtered,
washed with water and recrystallised from boiling water The acetamide ether of
orthonitrobenzoic acid thus obtained forms colourless crystals, melting at 115°
to 116° C'.
EXAMPLE XI.
33-4 kilos. paianitrobenzoic acid are dissolved in 35 kilos. of potash containing
32 per cent. of KOH and 190 kilos. alcohol. The mixture is heated with 18 kilos.
of chloracetamide during 10 hours on the water bath in a vessel connected with a
reflux-condenser. It is then thrown into 1,000 litres of water, the reaction of the
liquid is made alkaline by addition of sodium carbonate, the separated crystals are
filtered, washed with water and recrystallised from diluted alcohol. The acetamide
ether of para-nitrobenzoic acid prepared in this way forms colourless crystals which
melt at 186°168° C.
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
olaim is :-
1. The herein described manufacture of compounds of acetamide by causing
chloracetamide to react with alkalı salts of phenols or carboxylic acids of the
aromatic series or with their substitution products.
2. The compounds of acetamide manufactured as above set forth.