CH190842A - Process for the preparation of (1-phenyl-2,3-dimethyl-5-pyrazolony1) -isopentyl-ketone. - Google Patents
Process for the preparation of (1-phenyl-2,3-dimethyl-5-pyrazolony1) -isopentyl-ketone.Info
- Publication number
- CH190842A CH190842A CH190842DA CH190842A CH 190842 A CH190842 A CH 190842A CH 190842D A CH190842D A CH 190842DA CH 190842 A CH190842 A CH 190842A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- dimethyl
- ketone
- isopentyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical compound CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims description 6
- SMUKODJVMQOSAB-UHFFFAOYSA-N 2-ethylbutanoyl chloride Chemical compound CCC(CC)C(Cl)=O SMUKODJVMQOSAB-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- VBZRNFTXJDVEJP-UHFFFAOYSA-N 4-[6-(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)-2,8-dimethyl-5-oxononan-4-yl]-1,5-dimethyl-2-phenylpyrazol-3-one Chemical compound C1(=CC=CC=C1)N1N(C(=C(C1=O)C(CC(C)C)C(=O)C(CC(C)C)C1=C(N(N(C1=O)C1=CC=CC=C1)C)C)C)C VBZRNFTXJDVEJP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims 1
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000126 substance Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RLFWWDJHLFCNIJ-UHFFFAOYSA-N Aminoantipyrine Natural products CN1C(C)=C(N)C(=O)N1C1=CC=CC=C1 RLFWWDJHLFCNIJ-UHFFFAOYSA-N 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960005222 phenazone Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- VIBJMOFTMSBLHJ-UHFFFAOYSA-N 1,5-dimethyl-4-(4-methylpentanoyl)-2-phenylpyrazol-3-one Chemical group C1(=CC=CC=C1)N1N(C(=C(C1=O)C(=O)CCC(C)C)C)C VIBJMOFTMSBLHJ-UHFFFAOYSA-N 0.000 description 1
- ONHAXVQTGDDANJ-UHFFFAOYSA-N 4-(3-oxopyrazole-4-carbonyl)pyrazol-3-one Chemical compound N1=NC(C(=C1)C(=O)C=1C(N=NC1)=O)=O ONHAXVQTGDDANJ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- -1 isovaleryl antipyrine Chemical compound 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
verfahren zur Darstellung von (1-Phenyl-2,3-dimethyl-5-pyrazolonyl)-isopentyl-keton. Setzt man 1-Phenyl-2,3-dimethyl-5-pyra- zolon mit Diäthylacetylchlorid bei Gegenwart säureabspaltender Mittel, wie Aluminium chlorid oder Zinkchlorid, um, so entsteht das (1-Phenyl-2,3-dimethyl-5-pyrazolonyl)-iso- pentyl-keton der Zusammensetzung:
EMI0001.0008
Zweckmässig wird in indifferenten Lösungs mitteln, wie Schwefelkohlenstoff oder Benzol, gearbeitet.
Das neue Keton stellt einen gut kristallisierten Stoff von F. 1320 dar, der sich aus Wasser umkristallisieren lässt.
Die Darstellung von Betonen analog vor stehendem Verfahren ist an sich bekannt. Es wird in dem Schrifttum bereits auf analoge Pyrazolonyl-keton hingewiesen. So wird in der deutschen Patentschrift Nr. 270487 das 1-Phenyl-2,3-dimetbyl-4-äceto-5-pyrazolon als Ausgangsstoff zur Herstellung von Antipyril- chinolin-carbonsäure verwendet und in den Berichten der deutschen Chemischen Gesell schaft 66 (1933), S. 926 sind das 4-n-Butyryl- antipyrin sowie das Isovaleryl-antipyrin be schrieben. Die pharmakologische Wirkung der letztgenannten Verbindungen ist jedoch nur schwach oder gar nicht vorhanden.
Dem gegenüber erwies sich das neue Beton als stark antipyretisch wirksam. Im Tierversuch (Kaninchen) war es in dieser Beziehung dem Ausgangsstoff 1-Phenyl-2,3-dimethyl-5-pyra- zolon um ein Vielfaches überlegen. <I>Beispiele:</I> 1. Zu 19 Teilen 1-Phenyl-2,3-dimethyl- 5-pyrazolon gibt man 13 Teile Diäthylacetyl- chlorid und 20 Teile Aluminiumchlorid bei Gegenwart von Schwefelkohlenstoff. Die Um setzung wird durch Erwärmen am Rückfluss- kühler beendet.
Sobald die Salzsäureentwick- lung aufgehört hat, verjagt man das Lösungs mittel im Vakuum und versetzt den Rück stand mit Eiswasser. Der sich anfangs ölig abscheidende neue Stoff erstarrt bald in tafelförmigen Kristallen. Aus Wasser um kristallisiert, bildet das (1-Phenyl-2,3-di- methyl-5-py#azolonyl)-isopentyl-keton glän zende Kristallschuppen vom F.<B>1320.</B>
2. 10 Teile 1-Phenyl-2,3-dimethyl-5-pyra- zolon werden mit 8 Teilen Diäthylacetyl- chlorid verrieben. Unter Rühren trägt man ganz langsam 10 Teile gepulvertes und frisch hergestelltes Aluminiumchlorid ein. Nach der Beendigung der Salzsäureentwicklung wird auf dem Wasserbade erwärmt. Den erkalteten Rückstand versetzt man mit Eiswasser und arbeitet ihn in der vorbeschriebenen Weise auf.
3. 10 Teile 1-Phenyl-2,3-dimethyl-5-pyrä- zolon werden mit 8 Teilen Diäthylacetyl- chlorid und $ Teilen Zinkchlorid im Ölbade langsam am Rückflusskühler erwärmt. Bei etwa 1450 setzt die Salzsäureentwicklung ein. Man hält auf dieser Temperatur, bis jene beendet ist und verarbeitet den Rück stand wie bei den vorigen Beispielen auf das neue Keton.
process for the preparation of (1-phenyl-2,3-dimethyl-5-pyrazolonyl) -isopentyl-ketone. If 1-phenyl-2,3-dimethyl-5-pyrazolone is reacted with diethyl acetyl chloride in the presence of acid-releasing agents such as aluminum chloride or zinc chloride, the result is (1-phenyl-2,3-dimethyl-5-pyrazolonyl) isopentyl ketone of the composition:
EMI0001.0008
It is expedient to use inert solvents such as carbon disulfide or benzene.
The new ketone is a well-crystallized substance of F. 1320 that can be recrystallized from water.
The representation of concretes analogous to the above method is known per se. Analogous pyrazolonyl ketone is already referred to in the literature. For example, in German Patent No. 270487, 1-phenyl-2,3-dimetbyl-4-aceto-5-pyrazolone is used as the starting material for the production of antipyrilquinoline-carboxylic acid and in the reports of the German Chemical Society 66 (1933 ), P. 926, 4-n-butyryl antipyrine and isovaleryl antipyrine are described. However, the pharmacological effect of the last-mentioned compounds is only weak or non-existent.
In contrast, the new concrete proved to be strongly antipyretic. In animal experiments (rabbits) it was far superior to the starting material 1-phenyl-2,3-dimethyl-5-pyrazolone in this respect. <I> Examples: </I> 1. 13 parts of diethyl acetyl chloride and 20 parts of aluminum chloride are added to 19 parts of 1-phenyl-2,3-dimethyl-5-pyrazolone in the presence of carbon disulfide. The reaction is ended by heating on the reflux condenser.
As soon as the development of hydrochloric acid has stopped, the solvent is expelled in a vacuum and the residue is mixed with ice water. The new substance, which initially separates out as an oily substance, soon solidifies in tabular crystals. Recrystallized from water, the (1-phenyl-2,3-dimethyl-5-py-azolonyl) -isopentyl-ketone forms shiny crystal flakes of F. 1320.
2. 10 parts of 1-phenyl-2,3-dimethyl-5-pyrazolone are triturated with 8 parts of diethylacetyl chloride. 10 parts of powdered and freshly prepared aluminum chloride are slowly introduced with stirring. After the evolution of hydrochloric acid has ceased, the mixture is warmed on the water bath. Ice water is added to the cooled residue and it is worked up in the manner described above.
3. 10 parts of 1-phenyl-2,3-dimethyl-5-pyrazolone are slowly heated on the reflux condenser in an oil bath with 8 parts of diethyl acetyl chloride and parts of zinc chloride. Hydrochloric acid begins to develop around 1450. It is held at this temperature until it has ended and the residue is processed as in the previous examples for the new ketone.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE190842X | 1935-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH190842A true CH190842A (en) | 1937-05-15 |
Family
ID=5725777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190842D CH190842A (en) | 1935-05-07 | 1936-04-04 | Process for the preparation of (1-phenyl-2,3-dimethyl-5-pyrazolony1) -isopentyl-ketone. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH190842A (en) |
-
1936
- 1936-04-04 CH CH190842D patent/CH190842A/en unknown
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