Manufacture of ẞ Cymidine CÊH ( CH2) Certain Camphors.
Year: 1892

page_text: Date of Application, 12th Nov., 1892
Complete Specification Left, 4th Aug., 1893-Accepted, 16th Sept., 1893
PROVISIONAL SPECIFICATION.
[Communicated from abroad by Messrs. HAARMANN & REIMER, Vanillin-Fabrik,
in Holzminden a/d Weser, in the German Empire.]
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Manufacture of ẞ Cymidine CÊH (CH¸ ÑH₂ CH₂)
Certain Camphors.
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from the Oxims of
I, CHARLES DENTON ABEL, of No. 28 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 that under the reaction of dilute
mineral acid, the oxims of the camphor species having the composition C₁,H₁, O,
which they have determined to be methyl-ketones, are transformed, after
separation of water into the hitherto unknown ẞ cymidine of the composition CH,
which yields carvacrol under exchange of the amido for the
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(CH, NH, C,H,)
hydroxyl group.
EXAMPLE.
The readily crystallisable oxims obtained in the usual manner from tansy-oil and
of which one melts at 50° C., are heated to boiling in alcoholic solution (100 parts
oxims to 300 parts alcohol) under gradual addition of a mixture of about 100 parts
sulphuric acid and 100 parts of alcohol of 50 per cent.
After the reaction has continued for two hours the mixture is diluted with water,
the unchanged oxim and regenerated camphor are extracted by means of ether, the
residue is concentrated by evaporation and the base produced is separated by means
of alkali.
The cymidine thus produced boils at from 118° to 121° under a pressure
of 15 mm. and forms a slightly yellowish oil which does not solidify in the cold.
In place of sulphuric acid, other mineral acids may be employed with like
success.
The same base may be obtained in the manner described from the oxims prepared
in the usual manner from the fractions of absinth-, sage-, and thuja-oils boiling
under a pressure of 14 mm. at from 80° to 90° C.
The cymidine is applicable for pharmaceutical purposes.
EXAMPLE.
The readily crystallisable oxims obtained in the usual manner from tansy-oil and
of which one melts at 50° C., are heated to boiling in alcoholic solution (100 parts
oxims to 300 parts alcohol) under gradual addition of a mixture of about 100 parts
sulphuric acid and 100 parts of alcohol of 50 per cent.
After the reaction has continued for two hours the mixture is diluted with water,
the unchanged oxim and regenerated camphor are extracted by means of ether, the
residue is concentrated by evaporation and the base produced is separated by means
of alkali.
The cymidine thus produced boils at from 118° to 121° under a pressure
of 15 mm. and forms a slightly yellowish oil which does not solidify in the cold.
In place of sulphuric acid, other mineral acids may be employed with like
success.
The same base may be obtained in the manner described from the oxims prepared
in the usual manner from the fractions of absinth-, sage-, and thuja-oils boiling
under a pressure of 14 mm. at from 80° to 90° C.
The cymidine is applicable for pharmaceutical purposes.
ABEL & IMRAY,
Agents for the Applicant.
COMPLETE SPECIFICATION.
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from the Oxims of
Manufacture of ẞ Cymidine C.H¸ (CH3 NH₂ C3H7)
Certain Camphors.
I, CHARLES DENTON ABEL, 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 foreign correspondents have discovered that under the reaction of dilute
mineral acid the oxims of the camphors of the formula C10 H₁ O, which act as

page_text: methyl-ketones RCO CH, (K signifying in this formula an organic radical) are
transformed after separation of water, into the hitherto unknown 3-cymidine,
which yields carvacrol under exchange of the amido for the hydroxyl group.
EXAMPLE.
The crystallisable oxims obtained in the usual manner from tansy-oil and of
which one melts at 50° C., are heated to boiling in alcoholic solution (100 parts
oxims to 300 parts alcohol) under gradual addition of a mixture of about 100 parts
sulphuric acid and 100 parts of alcohol of 50 per cent.
After the reaction has continued for two hours the mixture is diluted with
water, the unchanged oxim and regenerated camphor are extracted by means of
ether, the aqueous solution is concentrated by evaporation and the base produced is
separated by means of alkali.
The B-cymidine thus produced boils at from 118° to 121° C. under a pressure
of 15 mm. and forms a slightly yellowish oil which does not solidify in the ordinary
freezing mixtures.
In place of sulphuric acid, other nineral acids may be employed with the same
success.
The same base may be obtained in the manner described from the oxims prepared
in the usual manner from the fractions of absinth-, sage, and thuja-oils boiling
under a pressure of 14 mm. at from 80° to 90° C.
This substance is applicable for pharmaceutical purposes, for preparing remedies
of antifebric action and for manufacturing colours.
Having now particularly described and ascertained the nature of my said inven-
tion and in what manner the same is to be performed I declare that what I
claim is :-
―:
1. The above described process for manufacturing 3 cymidine consisting in
boiling the oxims of the above defined camphor series with dilute acids in presence
of alcohol, diluting with water, extracting with ether for the separation of
unchanged oxims and regenerated camphors, evaporating the extracted aqueous
solution, and setting free the formed ẞ-cymidine by an alkali.
2. As a new product the B-cymidine prepared by the preceding process, boiling
under a pressure of 13 mm. at a temperature of from 118° to 121° C., having
specific weight of 0.9442, the composition C₁, A1, N and the constitutional formula: