CH240069A - Process for the preparation of a salt from antipyrine salicylate. - Google Patents
Process for the preparation of a salt from antipyrine salicylate.Info
- Publication number
- CH240069A CH240069A CH240069DA CH240069A CH 240069 A CH240069 A CH 240069A CH 240069D A CH240069D A CH 240069DA CH 240069 A CH240069 A CH 240069A
- Authority
- CH
- Switzerland
- Prior art keywords
- salt
- antipyrine
- antipyrine salicylate
- preparation
- salicylate
- Prior art date
Links
- WQAQKERCWPUIMH-UHFFFAOYSA-N 1,5-dimethyl-2-phenylpyrazol-3-one;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1O.CN1C(C)=CC(=O)N1C1=CC=CC=C1 WQAQKERCWPUIMH-UHFFFAOYSA-N 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 title claims description 5
- 239000011780 sodium chloride Substances 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229960003563 Calcium Carbonate Drugs 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000001225 therapeutic Effects 0.000 claims 1
- 239000002244 precipitate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VEQOALNAAJBPNY-UHFFFAOYSA-N Phenazone Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960005222 phenazone Drugs 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 229940091110 Antipyrine Drugs 0.000 description 2
- 229960005069 Calcium Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical group OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N Sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K Iron(III) chloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JYUXOLTYMOTEFQ-UHFFFAOYSA-N calcium;2-hydroxybenzoic acid Chemical compound [Ca].OC(=O)C1=CC=CC=C1O JYUXOLTYMOTEFQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000000126 substance Substances 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
Description
Verfahren zur Herstellung eines Salzes aus Antipyrinsalieylat. Obgleich bekannt ist, dass das sogenannte Antipyrinsalicylat (Antipyrinumsalicylicum) saure Eigenschaften besitzt, so sind doch Salze dieses Stoffes bisher nicht dargestellt worden. Gegenstand des vorliegenden Paten tes ist ein Verfahren zur Herstellung eines Salzes aus Antipyrinsalicylat, welches da durch gekennzeichnet ist, dass man auf Anti- pyrinsalicylat Kalziumcarbonat einwirken lässt.
<I>Beispiel:</I> Man erhitzt 65,2g Antipyrinsalicylat mit 1 Liter Wasser und etwa 10 g Kalziumcarbo- nat unter Aufrechterhaltung schwach saurer Reaktion, bis alles Antipyrinsalicylat in Lö sung gegangen ist, und filtriert heiss. Beim Erkalten erhält man die Kristalle des anti- pyrinsalicylsauren Kalziums. Aus der nach Abfiltrieren des Niederschlags erhaltenen Flüssigkeit erhält man durch Einengen wei tere Mengen der genannten Verbindung.
Das so dargestellte antipyrinsalicylsaure Kalzium bildet farblose kristallinische Schollen, löslich in etwa 20 Teilen Wasser (25 ), leichter lös lich in siedendem Wasser, auch in Weingeist löslich. Die Zusammensetzung der Verbin- dung entspricht der Formel Ca(Cl$H1704N_)z. Die wässrige Lösung der Verbindung gibt mit Säuren (Salzsäure, Essigsäure) Niederschläge, die sich im TJberschuss der ,Säuren lösen;
ein später sich bildender Niederschlag ist Salicyl- säure; mit Ferrichlorid gibt die Lösung einen dunkelbraunen Niederschlag. Die mit Salz säure versetzte Lösung gibt mit Natrium nitrat Grünfärbung (Antipyrin). Die ammo- niakalische Lösung gibt mit Ammonoxalat eine Fällung von Kalziumogalat.
Process for the preparation of a salt from antipyrin salylate. Although it is known that the so-called antipyrine salicylate (Antipyrinumsalicylicum) has acidic properties, salts of this substance have not yet been shown. The subject matter of the present patent is a process for the production of a salt from antipyrine salicylate, which is characterized in that the antipyrine salicylate is allowed to act on calcium carbonate.
<I> Example: </I> 65.2 g of antipyrine salicylate are heated with 1 liter of water and about 10 g of calcium carbonate while maintaining the weakly acidic reaction until all of the antipyrine salicylate has dissolved, and the mixture is filtered hot. When it cools down, the crystals of antipyrine salicylic acid calcium are obtained. From the liquid obtained after filtering off the precipitate, further amounts of the compound mentioned are obtained by concentration.
The antipyrinsalicylic acid calcium thus represented forms colorless crystalline clods, soluble in about 20 parts of water (25), more easily soluble in boiling water, also soluble in alcohol. The composition of the compound corresponds to the formula Ca (Cl $ H1704N_) z. The aqueous solution of the compound and acids (hydrochloric acid, acetic acid) give precipitates which dissolve in excess of the acids;
a precipitate that forms later is salicylic acid; with ferric chloride, the solution gives a dark brown precipitate. The solution mixed with hydrochloric acid gives a green color (antipyrine) with sodium nitrate. The ammoniacal solution and ammonoxalate precipitate calcium ogalate.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH240069T | 1944-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH240069A true CH240069A (en) | 1945-11-30 |
Family
ID=4461603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH240069D CH240069A (en) | 1944-01-26 | 1944-01-26 | Process for the preparation of a salt from antipyrine salicylate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH240069A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2472565A1 (en) * | 1979-11-09 | 1981-07-03 | Toho Pharma Co Ltd | N - ((ISOPROPYL-4-METHYL-2-PHENYL-1-PYRAZOLONE-5-YL-3) METHYL) ACETOXY-2-BENZAMIDE, PROCESS FOR PREPARING THE SAME, AND MEDICAMENTS CONTAINING THE SAME |
-
1944
- 1944-01-26 CH CH240069D patent/CH240069A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2472565A1 (en) * | 1979-11-09 | 1981-07-03 | Toho Pharma Co Ltd | N - ((ISOPROPYL-4-METHYL-2-PHENYL-1-PYRAZOLONE-5-YL-3) METHYL) ACETOXY-2-BENZAMIDE, PROCESS FOR PREPARING THE SAME, AND MEDICAMENTS CONTAINING THE SAME |
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