The Manufacture or Production of New Imido Compounds containing Halogen.
Year: 1898

page_text: The process proceeds in an analogous manner, if succinimide, ortho sulpho benzoic
imide, or similar imido compounds, are used in place of the phthalimide employed in
the above example. The caustic soda therein prescribed may be replaced by
the corresponding quantity of caustic potash or the like. Naturally, the
metallic salts of imides, such as the alkaline, earth-alkaline, or metal salts, can be
directly used, and brought into reaction with the halogens. Instead of water used in
the above example, "indifferent" solvents, such as benzene, chloroform, carbontetra-
chloride, or the like, can be employed; in which case the process can be carried out
at more elevated temperatures. The other halogen compounds, such as the chlorine
and iodine derivatives, are obtained in the same way, if chlorine or iodine are allowed
to act on the metallic salts of the herein before defined imido compounds.
My foreign correspondents wish it to be understood that they do not limit them-
selves to the directions given in the above example, which is merely typical, as the
present invention in general relates to the production of halogen derivatives contain-
ing the group
NX (X meaning chlorine, bromine, iodine, or the like) from
phthalimide, succinimide, orthosulpho benzoic imide, or the like imido compounds,
by the action of halogens on the metallic salts of the herein before-defined imido
compounds.
NEWTON & SON,
Agents for the Applicant.
COMPLETE SPECIFICATION.
The Manufacture or Production of New Imido Compounds
containing Halogen.
I, HENRY EDWARD NEWTON, of the Office for Patents, 6, Bream's Buildings,
Chancery Lane, in the County of London, 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 foreign correspondents have found that by the action of halogens on the
metallic salts of phthalimide, or the like imides, such as succinimide or ortho-
sulphobenzoic imides, hitherto unknown halogen compounds containing halogen
in place of the hydrogen of the imido group, can be easily produced, and the
researches of my foreign correspondents have further shown that these halogen
compounds are not only of value, in that they can be used as bases for the
preparation of other substances, but also inasmuch as they possess strong bactericide
properties, and they therefore constitute excellent antiseptics, for example in the
case of skin diseases.
The production of the above defined halogen compounds is, in general, effected
by allowing halogens to act on the metallic salts of phthalimide or the like.
In order to illustrate this process more fully, the following Example A is given,
the parts being by weight.

page_text: CO
at once separates. It is filtered off, carefully washed with ice-water, and dried at
low temperatures. If necessary, it may be further purified by crystallisation, using
"indifferent" solvents, such as benzene, chloroforin, carbon tetrachloride, ethyl-
acetate, or the like. For instance, by a re-crystallisation from benzene, it is obtained
as a slightly yellowish crystalline powder.
The process proceeds in an analogous manner if succinimide, orthosulphobenzoic-
imide, or similar inido compounds, are used in place of the phthalimide employed in
the above example. The caustic soda therein prescribed may be replaced by the
corresponding quantity of caustic potash or the like. Naturally, the metallic salts
of imides, such as the alkaline, earth alkaline, or metal salts, can be directly used, and
brought into reaction with the halogens. Instead of water used in the above example,
"indifferent" solvents, such as benzene, chloroform, carbon-tetrachloride, or the like,
can be employed, in which case the process can be carried out at more elevated
temperatures. The other halogen compounds, such as the chlorine and iodine
derivatives, are obtained in the same way, if chlorine or iodine are allowed to act on
the metallic salts of the hereinbefore defined imido compounds.
It may be remarked that in obtaining the production of the iodine compounds, it
is desirable to take care that the potassium iodide which is formed during the reaction
is directly removed, because the new iodine compounds combine very easily with the
potassium iodide, forming black-coloured double compounds. According to the
researches of my foreign correspondents, the formation of these double compounds
can be avoided by performing the reaction in the presence of chlorine or bromine, or
by employing, instead of the free iodine, the known compounds obtainable from
iodine and chlorine or bromine, such as ICI, ICI, IBr, or the like.
In order to illustrate this method of proceeding, the following Example B is given,
the parts being by weight.
EXAMPLE B.
A solution prepared from 86 parts of iodine, 56 parts of bromine, 100 parts of
sodium bromide, and 500 parts of water, is slowly introduced with stirring into an
icy-cold solution prepared from 100 parts of phthalimide, 32 parts of sodium hydroxide,
and 7000 parts of water. The iodine derivative from phthalimide thus produced
separates in the shape of a white precipitate during the reaction. It is filtered off,
washed, and dried at ordinary temperature. By a recrystallisation from benzene
or chloroform, the new compound is obtained in the shape of colourless crystals.
My foreign correspondents wish it to be understood that they do not limit them-
selves to the directions given in the above example, which is merely typical as the
present invention, in general, relates to the production of halogen derivatives con-
taining the group = (x meaning chlorine, bromine, iodine, or the like) from
phthalimide, succinimide, orthosulphobenzoic imide, or the like imido compounds,
by the action of halogens on the metallic salts of the hereinbefore defined imido
compounds.
Having now particularly described and ascertained the nature of the said
invention and in what manner the same is to be performed as communicated to me
from abroad, I declare that what I claim is :-
1. The process for producing new halogen derivatives from phthalimide or the like
imides, such as succinimide, orthosulpho benzoic imide, or the like (which derivatives

page_text: contain the halogen in place of the hydrogen of the imido group), by causing halogens
to act on the metallic salts of the imides substantially as hereinbefore described.
2. As new articles of manufacture, the new halogen compounds obtainable according
to the process herein before described and claimed.
3. The use of the new compounds, claimed in the foregoing Claim 2 for medicinal
purposes.