DE122287C - - Google Patents
Info
- Publication number
- DE122287C DE122287C DENDAT122287D DE122287DA DE122287C DE 122287 C DE122287 C DE 122287C DE NDAT122287 D DENDAT122287 D DE NDAT122287D DE 122287D A DE122287D A DE 122287DA DE 122287 C DE122287 C DE 122287C
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- alcohol
- thiopyrazolone
- dimethyl
- methyl
- 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
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910052976 metal sulfide Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M Potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- ZZOWFLAMMWOSCG-UHFFFAOYSA-N 5-chloro-3-methyl-1-phenylpyrazole Chemical compound N1=C(C)C=C(Cl)N1C1=CC=CC=C1 ZZOWFLAMMWOSCG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- -1 sulfur metals Chemical class 0.000 description 1
- 238000010792 warming 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
- C07D231/18—One oxygen or sulfur atom
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
M 122287 KLASSE Ϊ2ρ. M 122287 CLASS Ϊ2ρ.
Durch Einwirkung von wässerigem oder besser alkoholischem Alkali auf ein Halogenmethylat des i-Phenyl-^-methyl-s-chlorpyrazols, z. B. C11 H12 N2 Cl2, entsteht nach den Untersuchungen von Michaelis und Pasternach (Berichte d. D. ehem. Gesellsch. 32, 2398) ι -Phenyl-2,3-dimethyl- 5 -pyrazolon. In ähnlicher Weise bildet sich nun auch durch Einwirkung von Schwefelmetall oder Metallsulfhydrat, auf das genannte Chlorid (Bromid oder Jodid) ein Thiopyrazolonderivat C11 H12 N2 S. Es entsteht bei Anwendung von Kaliumsulfhydrat z. B. nach der Gleichung:By the action of aqueous or better alcoholic alkali on a halogen methylate of i-phenyl - ^ - methyl-s-chlorpyrazole, z. B. C 11 H 12 N 2 Cl 2 , arises according to the investigations by Michaelis and Pasternach (reports d. D. Former Gesellsch. 32, 2398) ι -phenyl-2,3-dimethyl-5-pyrazolone. In a similar way, a thiopyrazolone derivative C 11 H 12 N 2 S is formed by the action of sulfur metal or metal sulfhydrate on said chloride (bromide or iodide). B. according to the equation:
CnH12N2Cl2 + 2 KS H = C n H 12 N 2 Cl 2 + 2 KS H =
C11 H12 N2 S +2 KCl + H2S.C 11 H 12 N 2 S +2 KCl + H 2 S.
Das Chlormethylat des 1 -Phenyl- 3 -methyl-S-.chlorpyrazols C11H12N2Cl2 wird in Alkohol gelöst und mit der gleichen Gewichtsmenge Alkalisulfhydrat, z. B. Kaliumsulfhydrat, ebenfalls in Alkohol gelöst, allmählich versetzt. Unter lebhafter Reaction scheidet sich alsdann Chlorkalium aus und es entwickelt sich Schwefelwasserstoff. Nach kurzem Erwärmen auf dem Wasserbad entfernt man durch Einleiten von Kohlensäure oder durch Zusatz von Mineralsäuren das überschüssige Schwefelmetall, verdampft (bei Zusatz von Mineralsäuren unter Hinzufügen von Soda) zur Trockne und zieht «den Rückstand mit Alkohol aus. Es geht dann das Thiopyrazolonderivat in Lösung, während die anorganischen Salze zurückbleiben. Das beim Abdestilliren oder Verdampfen des Alkohols hinterbleibende Product wird aus Alkohol unter Zusatz von Aether oder aus heifsem Wasser umkrystallisirt. Es entsteht aus den Halogenmethylaten des 1 - Phenyl - 3 - methyl-5-chlorpyrazols auch in wässeriger Lösung und unter Anwendung von anderen Schwefelmetallen.The chloromethylate of 1-phenyl-3-methyl-S-.chlorpyrazole C 11 H 12 N 2 Cl 2 is dissolved in alcohol and treated with the same amount by weight of alkali metal sulfhydrate, e.g. B. potassium sulfhydrate, also dissolved in alcohol, gradually added. With a vigorous reaction, potassium chloride is then separated out, and hydrogen sulphide is evolved. After briefly warming up on the water bath, the excess sulfur metal is removed by introducing carbon dioxide or by adding mineral acids, evaporating to dryness (with the addition of mineral acids by adding soda) and extracting the residue with alcohol. The thiopyrazolone derivative then goes into solution, while the inorganic salts remain. The product which remains when the alcohol is distilled off or evaporated is recrystallized from alcohol with the addition of ether or from hot water. It arises from the halomethylates of 1 - phenyl - 3 - methyl-5-chloropyrazole, also in aqueous solution and when other sulfur metals are used.
Ersetzt man bei obigem Beispiel das Chlormethylat durch Brom oder Jodmethylat, so genügt es, auf 1 Gewichtstheil des Halogenmethylats 0,75 bis 0,60 Gewichtstheile Kaliumsulfhydrat anzuwenden.If in the above example the chloromethylate is replaced by bromine or iodine methylate, so it is sufficient to add 0.75 to 0.60 parts by weight of potassium sulfhydrate to 1 part by weight of the halomethylate apply.
Das i-Phenyl-2, 3-dimethyl-5-thiopyrazolon C11 H12 N2 S bildet dicke weifse Krystalle, die bei 166° schmelzen und mäfsig leicht löslich in Wasser, leicht löslich in Alkohol, sehr schwer löslich in Aether sind. Es ist wie das ι - Phenyl - 2, 3 - dimethyl - 5 - pyrazolon eine schwache Base und bildet z. B. ein schön krystallisirendes salzsaures Salz.The i-phenyl-2,3-dimethyl-5-thiopyrazolone C 11 H 12 N 2 S forms thick white crystals which melt at 166 ° and are moderately soluble in water, slightly soluble in alcohol, very sparingly soluble in ether. Like ι - phenyl - 2, 3 - dimethyl - 5 - pyrazolone, it is a weak base and forms z. B. a nicely crystallizing hydrochloric acid salt.
Das i-Phenyl-2, 3-dimethyl-5-thiopyrazolon soll in der Medicin Anwendung finden.The i-phenyl-2,3-dimethyl-5-thiopyrazolone should be used in medicine.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE122287C true DE122287C (en) |
Family
ID=391220
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT122287D Active DE122287C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE122287C (en) |
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0
- DE DENDAT122287D patent/DE122287C/de active Active
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