The Manufacture or Production of New Bases and Salts thereof, Containing Sulphur, from Dithiobiurets.
Year: 1892

page_text: Date of Application, 17th Aug., 1892
Complete Specification Left, 17th May, 1893-Accepted, 22nd July, 1893
PROVISIONAL SPECIFICATION.
[Communicated from abroad by THE FARBENFABRIKEN vormals FRIEDRICH
BAYER & Co., of Elberfeld, in the Empire of Germany.]
The Manufacture or Production of New Bases and Salts thereof,
Containing Sulphur, from Dithiobiurets.
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 to be as follows:-
Glutz has first described in Liebig's Annalen, volume 154, page 44, the so-called
phenyldithiobiuret, which he obtained by heating aniline with persulfocyanic acid.
The reaction taking place corresponds to the equation :

page_text: capability of the aforesaid dithiobiurets existing in two different structural forms,
viz., in the one as usually presumed :
formula:
RN = C (SH) NHC (SH) = NH.
The latter formula corresponds to a dimercaptane, and, in accordance therewith,
my foreign correspondents have found, that the dithiobiurets are oxidised by
means of the different oxidising agents to form disulphides, the two sulphur atoms
of the same molecule being connected one with the other, the said disulphides
being therefore monomolecular compounds.
In order to effect the oxidation, the most different chemical compounds can be
employed, viz., both such as give off oxygen, and such as cause oxygen to be
developed from other substances.
The following examples are given in order to illustrate the carrying out
practically of this invention. The parts are by weight.
OXIDATION OF
FIRST EXAMPLE.
IN ALCOHOLIC SOLUTION BY,
ALPHAPHENYLDITHIOBJURET
MEANS OF IODINE.
Two parts of phenyldithiobiuret are mixed with alcohol, or dissolved therein,
and iodine is added, employing the latter either in solid form or in solution. The
color of the iodine added disappears, and as soon as the mixture or solution
assumes a lasting yellowish brown color, the oxidation is completed.
About
2.5 parts of iodine are necessary for this purpose, which quantity corresponds to
2 atoms of iodine for one molecule of dithiobiuret.
On cooling the above alcoholic solution, a new compound, containing hydroiodic-
acid, separates in yellowish crystals, which melt at 104 degrees centigrade, and, as
my foreign correspondents have ascertained by analytical research, possess the
following composition :
CHN C
TIL
2
in combination with ethylalcohol. The aforesaid hydroiodic salt dissolves in
about 33 parts of cold alcohol, and in about 200 parts of cold water. On adding
diluted alkali-lye to the cold solution of hydroiodic salt in water, however without
employing an excess of alkali, the free base, viz. the disulphide of the formula,
separates. My foreign correspondents have ascertained by analytical research, and
by testing the molecular weight, that the disulphide in free state possesses the
composition: CH,N,S,.
This basic compound, which is termed "thiuret" by my correspondents, separates
out of its watery solutions in combination with so-called crystal water, which
can be removed by repeatedly treating it with strong alcohol, and subsequently
drying the product thus treated in vacuo, over sulphuric acid. The thiuret
readily dissolves in strong cold alcohol, and crystallises out of this solvent (when
its solutions are allowed to evaporate spontaneously) in glass-like brilliant. yellow
crystals, which contain crystal alcohol, and will readily give off the said alcohol.

page_text: The thiuret containing no water and alcohol, melts at 146 degrees centigrade
with decomposition. A product perfectly dried was analysed, and the result thus
obtained corresponds with the formula C,H,N,S,. On boiling its solution in
alcohol, it is decomposed, sulphur being separated. A similar alteration takes
place when it is brought into a longer contact with alkalies, or heated with
concentrated hydrochloric acid in closed tubes at 150 degrees centigrade.
It is not necessary to carry out the oxidation in alcoholic solution.
above mentioned hydroiodic salt of the "thiuret," containing crystal alcobol,
can be obtained in watery solution as described in the following example :-
-
The
OXIDATION OF
ALPHAPHENYLDITHIOBIURET
MEANS OF IODINE.
IN WATERY SOLUTION, BI
The alpha phenyldithiobiuret finely pulverised is mixed with water, and the
calculated quantity of iodine is added. The product resulting is boiled with
water, filtered off, and the yellowish needle-like crystalline mass is crystalised out
of alcohol.
If the phenyldithiobiuret employed in the foregoing two examples, be replaced
by other alkyldithiobiurets, or substitution products thereof, the corresponding
alkyldisulphides, which contain two hydrogen atoms less than the original alkyl-
dithiobiurets, are obtained in the same manner. For example, in employing
2.15 parts of ortho- or paratolyldithiobiuret, or 2-3 parts of metaxylyldithiobiuret
in the above first example, the hydroiodic salts of ortho- and paradimethylthiuret
aud dimethylthiuret, result in an analogous manner. These products, and the
analogous thiurets, and substituted thiurets, are similar to the real "thiuret
obtained from alphaphenyldithiobiuret.
"
On employing, in place of iodine, as described in the above first example, an
equivalent quantity of bromine or chlorine, viz., on treating the alkyldithiobiurets
or the substitution products thereof with bromine or chlorine, the hydrobromic
and hydrochloric salts of the thiuret, its homologues, analogues, and substitution
products thereof, are obtained substantially in the same manner.
"
The hydrobromic salt of "thiuret,' for example, is of the composition
CH,NS, + HBr + C,H,OH, and melts at 253 degrees whilst the hydrochloric
salt of the real "thiuret corresponds to the formula C.H,N,S, + HCl +
"
C,H,OH, and melts at 214 degrees centigrade.
In order to illustrate how to effect the oxidation by means of other oxidising
agents, the following examples are given, the parts being by weight.
THIRD EXAMPLE.
OXIDATION OF ALPHAPHENYLDITHIOBIURET BY MEANS OF HYDROGEN
DIOXIDE..
Phenyldithiobiuret is mixed with diluted hydrochloric acid, and after adding
the calculated quantity of a solution in water of hydrogen dioxide, the liquid is
allowed to stand for 24 hours. The mixture then is heated to boiling, and,

page_text: FIFTH EXAMPLE.
OXIDATION OF ALPHAPHENYLDITHIOBIURET WITH POTASSIUM FERRICYANIDE.
On adding to a solution of phenyldithiobiuret in ammonia, mixed with
ammonium chloride, an excess of potassium ferricyanide, a precipitate of thiuret
separates immediately.
The oxidation of alkyldithiobiurets, substitution products, and analogues thereof,
which are herein before defined, is not at all restricted to the examples above
mentioned, for this process likewise can be effected by means of other oxidising
agents, such as, for example, hypermanganic acid, chromic acid, or the like. The
methods which are to be used in employing such or like oxidising agents result
from the above examples in a simple manner.
The salts of thiurets containing no alcohol are produced by dissolving the
thiurets and analogous compounds in the acid desired, and by allowing the
solutions thus prepared to crystalise.
Out of the series of the salts containing alcohol, the hydrochlorate of thiuret
melts at 214 degrees centigrade, the hydrobromic salt at 253 degrees centigrade,
and the hydroiodic salt at 104 degrees centigrade.
My foreign correspondents have also prepared other salts of " thiuret," for
example, the borate, melting at 114 degrees, the salicylate melting at 76 degrees
centigrade, the ortho cresotinic salt melting at 75 degrees, the phenolsulphonic salt
melting from about 215 to 216 degrees centigrade.
On dissolving, for example, thiuret in glacial acetic acid, the corresponding
acetate of thiuret is formed, and it is noticeable that the determination of the
molecular weight of the said acetate in glacial acetic acid by means of Raoult's
method, yielded the proportion 241, whilst the theoretical molecular weight
amounts to 263. Hence follows, that the thiuret, and likewise its analogues,
homologues and substitution derivatives, represent monomolecular compounds, and
in no wise have been formed by the combination of two molecules of alkyldithio-
biuret, or the like, during the oxidation process.
Of course, in the employment of methylalcohol, propylalcohol, butylalcohol,
amylacohol, and the like, as solvents or diluents, the analogous salts containing the
respective alcohol, as so called crystal alcohol, are produced.
All these salts containing crystal alcohol which have been ascertained by
analytical research, show the following reactions, which are likewise in accordance
with the existence of alcohol in these products:-
Firstly. By crystalising the hydroiodic salts of thiurets containing methyl-
alcohol out of ethylalcohol, the corresponding hydroiodic salts containing
ethylalcohol in place of methylalcohol are formed, and inversely.
Secondly. The halogen acid salts containing alcohol give off alcohol when
mixed with cold water, and are transformed into such as contain water in place
of alcohol.
Thirdly. On boiling the hydroiodic salts of thiurets containing alcohol with the
addition of concentrated hydrochloric acid, the respective hydrochloric salts
containing water in place of alcohol, result.
"
On the addition of diluted alkalies to the cold solutions of the salts of thiurets
and analogous compounds, the free bases, viz., "thiurets are separated.
Amongst the homologues of the above "thiuret," derived from alphaphenyl-
dithiobiuret, those products especially are of value which are obtained from
paratolyldithiobiuret, orthotolyldithiobiuret, and metaxylyldithiobiuret, and

page_text: which, in accordance with the "thiuret" resulting from phenyldithiobiuret, are
termed paramethylthiuret, orthomethylthiuret, and dimethylthiuret.
These thiurets, in general, are similar to the real "thiuret," and yield analogous
salts, viz., hydrochlorates, hydroiodates, hydrobromates, borates, plienylsulfonates,
salicylates, cresotinic salts, and the like, which likewise are similar to the above
named salts of "thiuret" obtained from phenyldithiobiuret.
The other homologues of "thiuret," the analogous products derived from alkyl-
dithiobiurets of the fatty series, and the thiurets obtained from the substitution
products of fatty or aromatic alkyldithiobiurets, exhibit in general the same or
similar chemical properties as the real "thiuret," which is the type of all these
compounds, the production of which, by means of oxidation of alkyldithiobiurets,
substituted or not substituted, is the essential feature of this invention.
The thiurets, by which general name my foreign correspondents term all the
products obtained in carrying out this invention, are capable of being employed
either in free state, or in form of salts thereof, for therapeutical purposes, as
valuable disinfectants.
Dated this 17th day of August 1892.
NEWTON & SON,
Agents for the Applicant.
COMPLETE SPECIFICATION.
The Manufacture or Production of New Bases and Salts thereof,
Containing Sulphur, from Dithiobiurets.
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 :-
So-called phenyldithiobiuret was first described by Glutz in Liebig's Annalen
(volume 154, page 44). He obtained it by heating aniline with persulfocyanic
acid, the action taking place as represented by the equation :—

page_text: OXIDATION OF
ALPHAPHENYLDITHIOBIURET
MEANS OF IODINE.
IN ALCOHOLIC SOLUTION BY
2 parts of phenyldithiobiuret are mixed with alcohol, or dissolved therein, and
iodine is added, the latter being used either in the solid form or in solution. As
soon as the mixture or solution assumes a permanent yellowish brown colour, owing
to the iodine being in excess, the oxidation is completed. About 2.5 parts of
iodine are necessary for this purpose, the which quantity corresponds to 2 atoms of
iodine for one molecule of dithiobiuret.
On cooling the alcoholic solution, a new compound, containing hydrogen iodide,
separates in yellowish crystals, which melt at 104 degrees centigrade. My foreign
correspondents have ascertained that this possesses the composition represented by
the expression: CH,NS, + HI + C,H,OH.
The product thus obtained is the hydriodide of the disulphide—

page_text: the disulphide of the above formula, separates, on adding diluted alkali-lye to a
cold solution of the hydriodide in water, it being unnecessary to employ an excess
of alkali.
This basic compound, which is termed "thiuret" by my foreign correspondents,
separates from its solutions in water in combination with water of crystallisation,
which can be removed by repeatedly treating it with strong alcohol, and subse-
quently drying the product thus treated in vacuo over sulphuric acid. Thiuret
readily dissolves in strong cold alcohol, and crystallises from this solvent (on
spontaneous evaporation) in glass-like, brilliant yellow crystals, which contain
alcohol of crystallisation, which is readily given off.
Thiuret free from water and alcohol melts at 146 degrees centigrade, undergoing
decomposition. On boiling its solution in alcohol, it is decomposed, sulphur being
separated. A similar alteration takes place when it is allowed to remain for some
time in contact with alkalies, or is heated with concentrated hydrochloric acid in
closed tubes at 150 degrees centigrade.
It is not necessary to carry out the oxidation in alcoholic solution. The above
mentioned hydriodide of thiuret, containing alcohol of crystallisation, can be
obtained in aqueous solution as described in the following example ·
OXIDATION OF
ALPHAPHENYLDITHIOBIURET
MEANS OF IODINE.
IN AQUEOUS SOLUTION BY
The finely pulverised alphaphenyldithioburet having been mixed with water, the
calculated quantity of iodine is added. The resulting product is boiled with water,
filtered off, and the yellowish crystalline mass is crystallised from alcohol.
If the phenyldithiobiuret employed in the foregoing two examples be replaced by
other alkyldithiobiurets, or substitution products thereof, the corresponding alkyl-
disulphides, which contain 2 hydrogen atoms fewer than the original alkyl-
dithiobiurets are obtained in the same manner. For example, on employing
2.15 parts of ortho- or paratolydithiobiuret, or 2-3 parts of metaxylyldithiobiuret in
the above first or second example, the hydriodides of ortho- and paramethylthiuret
and dimethylthiuret are formed in an analogous manner. These products, and the
analogous thiurets and substituted thiurets, are similar to thiuret obtained from
alphaphenyldithiobiuret.
On employing, in place of iodine, as described in the above first example, an
equivalent quantity of bromine or chlorine, viz., on treating the alkyldithiobiurets,
or the substitution products thereof, with bromine or chlorine, the hydrobromide or
hydrochloride of thiuret, its homologues, analogues, and substitution products
thereof, are obtained substantially in the same manner.
The hydrobromide of thiuret, for example, is of the composition: CH,N,S, +
HBr C,H,OH, and melts at 253 degrees, whilst the hydrochloride of the thiuret
has the formula: C,H,N,S, + HCl + C,H,OH, and melts at 214 degrees
centigrade.
In order to illustrate the mode of effecting the oxidation by means of other
oxidising agents, the following examples are given, the parts being by weight:
THIRD EXAMPLE.
OXIDATION OF ALPHAPHENYLDITHIOBIURET WITH FERRIC CHLORIDE.
2 parts of alphanaphthyldithiobiuret are mixed with water and 3-3 parts of ferric
chloride, and the resulting liquid is heated to its boiling point. As soon as the
mixture exhibits a permanent yellowish color, the action is completed. The
resulting thinnat hedmachlida
the landl

page_text: OXIDATION OF ALPHAPHENYLDITHIOBIURET BY MEANS OF HYDROGEN
DIOXIDE.
Phenydithiobiuret is mixed with diluted hydrochloric acid, and, after adding the
calculated quantity of an aqueous solution of hydrogen dioxide, the liquid is
allowed to stand for 24 hours. The mixture is then heated to boiling, and filtered
whilst hot. The thiuret hydrochloride crystallises from the filtrate as it cools.
The hydrogen dioxide can be replaced by other dioxides acting in the same or a
similar manner, riz., barium dioxide, lead dioxide, manganese dioxide, or the like.
On adding to a solution of phenyldithiobiuret in ammonia mixed with ammonium
chloride, an excess of potassium ferricyanide, a precipitate of thiuret immédiately
separates.
The oxidation of alkyldithiobiurets, substitution products and analogues thereof,
which are hereinbefore defined, is in no way restricted to the examples above
mentioned, as this process can also be effected by means of other oxidising agents,
such as, for example, permanganic acid, chromic acid, or the like. The methods
which are to be used when employing such or like oxidising agents, are rendered
obvious by the above examples.
The salts of thiurets are produced free from alcohol by dissolving the thiurets
and analogous compounds in the corresponding diluted acid, and by allowing the
solutions thus prepared to crystallise.
My foreign correspondents have also prepared other salts of thiuret, for example,
the borate, inelting at 144 degrees, the salicylate, melting at 76 degrees centigrade,
the orthocresotinic salt, melting at 75 degrees, the phenolsulphonic salt, melting at
about 215 to 216 degrees centigrade.
On dissolving thiuret, for example, in glacial acetic acid, the corresponding
acetate of thiuret is formed, and it is noticeable that the determination of the
molecular weight of the said acetate in glacial acetic acid by means of Raoult's
method, gave, as result, the number 241, the theoretical molecular weight being 263.
Hence it follows, that thiuret, and also its analogues, homologues, and substitution
derivatives, occur as monomolecular compounds, and are in nowise formed by the
combination of two molecules of alkyldithiobiuret, or the like, during the oxidation
process.
If methylalcohol, propylalcohol, butylalcohol, amylalcohol, or the like, are used
as solvents or diluents, the analogous salts containing the alcohol used as alcohol of
crystallization are produced.
All these salts containing alcohol of crystallisation shew the following
behaviour.
Firstly. By crystallising the hydriodides of thiurets containing methylalcohol,
from ethylalcohol, the corresponding hydriodides containing ethylalcohol in place
of methylalcohol, are formed, and inversely.
Secondly. The haloid salts containing alcohol, give off alcohol when mixed with
cold water, and are transformed into such as contain water in place of alcohol.
Thirdly. On boiling the hydriodide of the thiurets containing alcohol with
concentrated hydrochloric acid, the hydriodides, containing water in place of
alcohol, are formed.
The salts of thiurets, such as the hydrochlorides, hydrobromides, or hydriodides,
are either directly obtained in cases in which the oxidation of alkyldithiobiurets is

page_text: effected in acid solution, or when acids are formed during the oxidation process, or
these and other salts (such as the borates, phenolsulphonates, salicylates, orthocreso-
tinates, and the like, are prepared by treating the bases with the necessary acids.
The borates, phenolsulphonates, salicylates, orthocresotinates, or the like salts, can
also be produced by treating the hydrochlorides, hydrobromides, or hydriodides, of
thiurets, with the alkaline salts of the corresponding acids (boric acid, phenol-
sulphonic acid, salycylic, cresotinic acid, or the like).
On adding diluted alkalies to the cold solutions of the salts of thiurets and
analogous compounds, the thiurets themselves are separated.
Of the homologues of thiuret derived from alpha-phenyldithiobiuret, those
products especially are of value which are obtained from paratolyldithiobiuret,
orthotolyldithiobiuret, and metaxylyldithiobiuret, and which, in accordance with
the system adopted in naming thiuret, are termed "paramethylthiuret," "ortho-
methylthiuret," and "dimethylthiuret."
These, and similar thiurets of the benzene or naphthalene series, in general, are
similar to thiuret, and yield analogous salts, viz., hydrochlorides, hydriodides,
hydrobromides, borates, phenylsulphonates, salicylates, cresctinates, and the like,
which also are similar to the above-named salts of thiuret obtained from
phenyldithiobiuret.
The properties of para-methylthiuret, ortho-methylthiuret, dimethylthiuret, and
the salts thereof, are hereinafter enumerated :
a) Para-methylthiuret. The base crystallizes from alcohol in prismatic cystals
of a pale yellow color, melting at 101 degrees centigrade. It is precipitated in the
form of voluminous white flakes by the addition of ammonia to a solution of the
hydrochloride. The latter salt forms beautiful prismatic cystals of a pale yellow
color, moderately soluble in water, and melting at 200 degrees centigrade. The
hydroidide forms yellowish crystals melting at 218 degrees, undergoing decom-
position thereby; it readily dissolves in alcohol, but less readily in water.
The borate is obtained as a white flaky precipitate soluble in water with
difficulty. The paraphenolsulphonate forms an amorphous mass. The salicylate
and the orthocresotinate are white precipatates soluble with difficulty; the former
melts at 114 degrees, whilst the latter melts at 116 degrees centigrade.
b) Ortho-methylthiuret. The base crystallises from alcohol in light grey
crystals readily soluble in alcohol, and melting at 87 degrees centigrade. The
hydrochloride forms white brilliant lamina moderately soluble in water, and melting
at 135 degrees centigrade, whilst the hydriodide easily dissolves in alcohol, and.
crystallises therefrom in yellow laminæ melting at 118 degrees centigrade.
The borate dissolves with difficulty in water, but readily in alcohol, and is
obtained as a white precipitate, melting at 123 degrees centigrade. The para-
phenolsulphonate forms an amorphous mass. The salicylate is obtained in the
form of a white flaky mass, which dissolves with difficulty in hot water, but with
very great ease in alcohol; it melts at about 90 degrees centigrade. The ortho-
cresotinate is a white flaky precipitate dissolving in water with difficulty, but in
alcohol with very great readiness; it melts at about 101 degrees centigrade.
(c) Dimethylthiuret. The base melts at 99 degrees centigrade. The hydro-
chloride forms light yellowish brown crystals, which dissolve in water with
moderate facility, and melts at 170 degrees centigrade. The hydriodide crystal-
lises from alcohol in yellowish white crystals readily soluble in alcohol, but soluble
with difficulty in water; it melts at 121 degrees centigrade. The borate is a white
precipitate soluble with difficulty. The paraphenolsulphonate forms an amorphous
mass. The salicylate and orthocresotinate form white precipitates, which can be
obtained in crystals from alcohol. The former melts at 83 degrees centigrade,.
whilst the latter melts at 87 degrees centigrade.
The other homologues of thiuret, the analogous products, and the thiurets.
obtained from the substitution products of alkyldithiobiurets, belonging to the
benzene or naphthalene series, exhibit, in general, chemical properties identical
with, or similar to, those of thiuret, which is the type of all the compounds, the
B

page_text: production of which, by the oxidation of substituted or unsubstituted alkyldithio-
biurets, is the essential feature of this invention.
Amongst the analogues or homologues or substitution derivatives of thiuret, for
instance, the alphanaphthyl derivative melts at 238 degrees centigrade; its hydri-
odide is a flaky mass melting at 251 degrees centigrade, and the corresponding 5
hydrochloride is a yellowish green powder melting at 228 degrees centigrade.
The "paraethoxythiuret hydrochloride,” having the formula :
forms needles of a greyish color, melting at 156 degrees centigrade.
The "thiurets," as my foreign correspondents term all the products obtained in
carrying out this invention, are capable of being employed either in the free state,
or in the form of salts, for therapeutical purposes, or as valuable disinfectants.
Having now particularly described and ascertained the nature of this inven-
tion and in what manner the same is to be performed, as communicated to me by
my foreign correspondents, I declare that what I claim is :-
1. The process for producing new basic disulphides (so-called "thiurets"), having
the general formula: R C,H₂N,S,, by treating alkyldithiobiurets of the general
formula R C,H,N,S,, with oxidising agents, in alkaline, neutral, or acid solution,
and in those cases in which acids either. are employed in effecting the oxidation,
or are formed during the oxidation, subsequently decomposing the resulting thiuret
salts by means of diluted alkalies, and isolating the bases in a suitable manner.
2. The production of thiuret, paramethylthiuret, orthomethylthiuret, dimethyl-
thiuret, or analogous alkylated thiurets of the benzene series, by oxidising phenyl-
dithiobiuret, paratolyldithiobiuret, orthotoyldithiobiuret, metaxylyldithiobiuret, or
analogous dithiobiurets of the benzene series, in alkaline, neutral, or acid solution,
and in those cases in which acids either are employed in effecting the oxidation, or
are formed during the oxidation process, decomposing the resulting thiuret salts
by means of diluted alkalies, and subsequently isolating the bases in a suitable
manner.
3. The production of alkylhydroxy thiurets of the general formula-R'OR
C,H,N,S, (such as ethoxythiuret), by oxidising alkylhydroxyphenyldithiobiurets
in accordance with the process defined in the foregoing first and second claims.
4. The process for producing thiurets of the naphthalene series, by treating
naphthyldithiobiuret with oxidising. agents, substantially in the mauner defined in
the preceding claims.
:
: 5. The production of salts of thiurets (such as the hydrochlorides, hydrobromides,
or hydroiodides, either be effecting the oxidation processes herein before defined, in
acid solutions, or in such manner that acids are formed during the oxidation, and
isolating the salts thus formed by a suitable process, or by converting the bases
formed by the above processes, by suitable treatment, into the required salts.
6. The process for producing borates of thiurets, either by treating the thiurets
of the benzene or naphthalene series with boric acid, or by acting with alkaline
salts of boric acid, on the salts of thiurets, and isolating the borates thus formed in
a suitable manner.
.
7. The production of organic salts of thiurets (such as phenolsulphonates,
salicylates, orthocresotinates, or the like), either by treating the thiurets of the
benzene or naphthalene series with organic acids (such as phenolsulpho acid,
salicylic acid, orthocresotinic acid, or the like), or by acting with the alkaline
salts of the last-named acids on the thiurets, and isolating the salts thus formed in
a suitable manner.

page_text: 8. As new manufactures, the thiurets of the benzene or naphthalene series.
(having the general formula R C,H,N,S,), and the salts thereof obtainable by
means of the processes hereinbefore defined, or in any other way, especially the
following products, having the properties hereinbefore described:
(a) Thiuret, paramethylthiuret, orthomethylthiuret, dimethylthiuret; the
hydrochlorides, hydrobromides, and hydriodides thereof, the borates,
phenolsulphonates, salicylates, and orthocresotinates derived from these
thiurets;
(b) Paraethoxythiuret hydrochloride;
8
Alphanaphthylthiuret, the hydrochloride and hydriodide thereof.
9. The employment of thiurets of the benzene or naphthalene series, and salts.
thereof, as disinfectants, or for other therapeutical purposes.
Dated this 16th day of May 1893.
NEWTON & SON,
Agents for the Applicant.