DE234631C - - Google Patents
Info
- Publication number
- DE234631C DE234631C DENDAT234631D DE234631DA DE234631C DE 234631 C DE234631 C DE 234631C DE NDAT234631 D DENDAT234631 D DE NDAT234631D DE 234631D A DE234631D A DE 234631DA DE 234631 C DE234631 C DE 234631C
- Authority
- DE
- Germany
- Prior art keywords
- base
- citric acid
- water
- dimethylamino
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000002585 base Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000004936 stimulating Effects 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- 239000004135 Bone phosphate Substances 0.000 description 1
- YUYFGUSFMDPGGJ-UHFFFAOYSA-N CN(C)N1N=CCC1=O Chemical compound CN(C)N1N=CCC1=O YUYFGUSFMDPGGJ-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- GUWSLQUAAYEZAF-UHFFFAOYSA-L Lead(II) acetate Chemical compound O1C(C)=O[Pb]21O=C(C)O2 GUWSLQUAAYEZAF-UHFFFAOYSA-L 0.000 description 1
- LWIHDJKSTIGBAC-UHFFFAOYSA-K Tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- HOQPTLCRWVZIQZ-UHFFFAOYSA-H bis[[2-(5-hydroxy-4,7-dioxo-1,3,2$l^{2}-dioxaplumbepan-5-yl)acetyl]oxy]lead Chemical compound [Pb+2].[Pb+2].[Pb+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HOQPTLCRWVZIQZ-UHFFFAOYSA-H 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- -1 dimethylamino- Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
- 238000005429 turbidity Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/46—Oxygen atom in position 3 or 5 and nitrogen atom in position 4
- C07D231/48—Oxygen atom in position 3 or 5 and nitrogen atom in position 4 with hydrocarbon radicals attached to said nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 234631 KLASSE 12p. GRUPPE- M 234631 CLASS 12p. GROUP
RUDOLF OTTO in FRANKFURTa. M.RUDOLF OTTO in FRANKFURTa. M.
Verfahren zur Darstellung von sekundärem, citronensaurem l-Phenyl-2 · S-dimethyl-^dimethylamino-ö-pyrazolon.Process for the preparation of secondary, citric acid l-phenyl-2 · S-dimethyl- ^ dimethylamino-ö-pyrazolone.
Das vorliegende Verfahren betrifft die Darstellung von sekundärem, citronensaurem i-Phenyl-2 · s-dimethyl^-dimethylamino-S-pyrazolon The present process relates to the preparation of secondary citric acid i-phenyl-2 · s-dimethyl ^ -dimethylamino-S-pyrazolone
C6 Ha O7 (C15H17O Na),.C 6 H a O 7 (C 15 H 17 ON a ) ,.
Das neue Salz wird erhalten, indem man ι Mol. Citronensäure auf 2 Mol. der Base mit oder ohne Zusatz von Wasser in der WärmeThe new salt is obtained by adding 1 mole of citric acid to 2 moles of the base or without the addition of water in the warmth
ίο einwirken läßt.ίο lets act.
Während die Salze des i-Phenyl-2 · 3-dimethyl-4-dimethylamino-5-pyrazolons mit ein- und .zweibasischen organischen Säuren sich leicht in einheitlicher kristallisierter Form gewinnen lassen, ist dies bei den drei theoretisch möglichen Salzen der Base mit der dreibasischen Citronensäure nicht der Fall.While the salts of i-phenyl-2 · 3-dimethyl-4-dimethylamino-5-pyrazolons with monobasic and .diibasic organic acids can easily be obtained in a uniform crystallized form let, this is the case with the three theoretically possible salts of the base with the tribasic Citric acid does not.
Das primäre Salz (aus gleichen Molekülen Base und Säure) bildet einen dicken Sirup, der erst nach vielen Wochen Kristalle abscheidet. Das tertiäre Salz (aus 3 Mol. Base und ι Mol. Säure) scheint sich mit Wasser zu dissoziieren, da es keine einheitlichen Kristalle bildet. Wegen des geringen Säuregehaltes kommt es für die therapeutische Verwendung nicht in Betracht.The primary salt (from the same base and acid molecules) forms a thick syrup, which only separates crystals after many weeks. The tertiary salt (from 3 mol. Base and ι mol. acid) seems to dissociate with water, since there are no uniform crystals forms. Because of the low acid content, it is used for therapeutic purposes out of consideration.
Dagegen kann das sekundäre Salz leicht und in guter Ausbeute in großen Kristallen erhalten werden und besitzt therapeutisch wertvolle Eigenschaften. Es soll nämlich, wie die zugehörige Base hauptsächlich als Antineuralgicum Verwendung finden. Die freie Base hat bekanntlich toxische Eigenschaften, besonders schwächende Wirkung aufs Herz.On the other hand, the secondary salt can easily and in good yield in large crystals and has therapeutically valuable properties. It's supposed to be how the associated base is mainly used as an antineuralgic. The free Base is known to have toxic properties, especially a debilitating effect on the heart.
4040
4545
Die Citronensäure dagegen wirkt belebend und anregend auf die Herztätigkeit, so daß in der neuen Verbindung die herzschädigende Wirkung der Base durch die anregende der Säure aufgehoben wird. Sie wird daher, wie durch Vergleichsversuche festgestellt wurde, selbst in großen Dosen gut vertragen und ist verhältnismäßig ungiftig. Ferner bedingt ihre größere Wasserlöslichkeit gegenüber der Base eine raschere Wirkung.Citric acid, on the other hand, has an invigorating and stimulating effect on the heart, so that in the new compound the heart-damaging effect of the base through the stimulating of the acid will be annulled. It is therefore, as has been established by comparative tests, even in Well tolerated in large doses and is relatively non-toxic. Furthermore, their greater water solubility compared to the base a faster effect.
Das unter dem Namen »Citrovanille« in den Handel gebrachte Präparat (vgl. Pharm. Centralhalle 44[1903J1 S. 911, und Hagers Handb. der Pharm. Praxis Ergänzungsb. 1908, S. 65) enthält in der Hauptsache das tertiäre, citronensäure Salz des i-Phenyl-2 · 3-dimethyl-4-dimethylamino-5-pyrazolons, welches wegen seiner Unbeständigkeit und seines geringen Gehaltes an Citronensäure, wie oben angeführt wurde, in therapeutischer Hinsicht wertlos ist.The preparation marketed under the name "Citrovanille" (cf. Pharm. Centralhalle 44 [1903J 1 p. 911, and Hagers Handb. Der Pharm. Praxis Zusatzb. 1908, p. 65) mainly contains the tertiary citric acid Salt of i-phenyl-2 · 3-dimethyl-4-dimethylamino-5-pyrazolone, which is of therapeutic value because of its instability and its low citric acid content, as stated above.
44 Gewichtsteile i-Phenyl-2 · 3-dimethyl-4~ dimethylamino-5-pyrazolon und 21 Teile Citronensäure werden mit 50 Teilen Wasser auf 750 erwärmt, wodurch klare Lösung eintritt. Nach ι bis 2 Tagen werden die großen Kristalle von der Mutterlauge abfiltriert, mit kaltem Wasser ausgewaschen und bei gewöhnlicher Temperatur getrocknet.44 parts by weight of i-phenyl-2 * 3-dimethyl-4 ~ dimethylamino-5-pyrazolone and 21 parts of citric acid are heated with 50 parts of water at 75 0 enters whereby clear solution. After ι to 2 days, the large crystals are filtered off from the mother liquor, washed with cold water and dried at ordinary temperature.
Man kann auch die Gewichtsmengen der Substanzen des Beispiels 1 ohne Wasser aufThe amounts by weight of the substances of Example 1 can also be used without water
5555
dem Wasserbad unter Rühren zusammenschmelzen. Beim Erkalten des Reaktionsproduktes erstarrt es zu einer kristallinischen Masse, die sich, falls erforderlich, aus wenig Wasser Umkristallisieren und pulverisieren läßt. Die Kristalle sind bedeutend leichter wasserlöslich als die Base selbst; sie lösen sich auch in Alkohol und sind schwerlöslich in Äther, Benzol und Chloroform. Ihr Schmelzpunkt liegt bei 85 ° C. Beim Erhitzen der Kristalle mit konzentrierter Schwefelsäure tritt eine lebhafte Entwicklung von Kohlenoxyd und Kohlensäure ein. Aus der wässerigen Lösung des Salzes fällt durch eine Lösung von Bleiacetat ein weißer Niederschlag von Bleicitrat, der sich in Ammoniak löst. Mit Eisenchlorid färbt sich die wässerige Lösung der neuen Verbindung ohne Trübung violett. Diese Färbung verschwindet aber nicht sogleich wie bei der Base, sondern bleibt längere Zeit bestehen. Melt together in the water bath while stirring. When the reaction product cools it solidifies to a crystalline mass, which, if necessary, consists of little Water recrystallize and pulverize. The crystals are significantly more soluble in water than the base itself; they also dissolve in alcohol and are sparingly soluble in ether, Benzene and chloroform. Their melting point is 85 ° C. When the crystals are heated with concentrated sulfuric acid there is a lively development of carbon dioxide and Carbonated one. From the aqueous solution of the salt falls through a solution of lead acetate a white precipitate of lead citrate that dissolves in ammonia. With ferric chloride the aqueous solution of the new compound turns violet without turbidity. This coloring but does not disappear immediately as with the base, but persists for a longer period of time.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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DE234631C true DE234631C (en) |
Family
ID=494476
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT234631D Active DE234631C (en) |
Country Status (1)
Country | Link |
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DE (1) | DE234631C (en) |
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- DE DENDAT234631D patent/DE234631C/de active Active
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