AT99014B - Process for the preparation of compounds of 4-dimethylamino-2,3-dimethyl-1-phenil-5-pyrazolone. - Google Patents
Process for the preparation of compounds of 4-dimethylamino-2,3-dimethyl-1-phenil-5-pyrazolone.Info
- Publication number
- AT99014B AT99014B AT99014DA AT99014B AT 99014 B AT99014 B AT 99014B AT 99014D A AT99014D A AT 99014DA AT 99014 B AT99014 B AT 99014B
- Authority
- AT
- Austria
- Prior art keywords
- pyrazolone
- dimethylamino
- dimethyl
- compounds
- phenil
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 claims description 4
- 229960002319 barbital Drugs 0.000 claims description 4
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 dipropyl- Chemical compound 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229960000880 allobarbital Drugs 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- RCOUWKSZRXJXLA-UHFFFAOYSA-N propylbarbital Chemical compound CCCC1(CCC)C(=O)NC(=O)NC1=O RCOUWKSZRXJXLA-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Verbindungen des 4, -Dimethylamino-2, 3-dimethyl- - l-phenil-5-pyrazolons.
Das Stammpatent Nr. 89936 betrifft ein Verfahren zur Darstellung einer Verbindung von 4-Dimethylamino-2, 3-dimethyl-l-phenyl-5-pyrazolon und Diäthylbarbitursäure, das darin besteht, dass man die beiden Komponenten zusammenschmilzt.
Wenn man gemäss vorliegender Erfindung von Homologen der Diäthylbarbitursäure ausgeht, wie Dipropyl-, Diallyl-, Phenyläthylbarbitursäure, und sie in gleicher Weise mit 4-Dimethylamino-2, 3- - dimethyl-l-phenyl-5-pyrazolon behandelt, so gelangt man ebenfalls zu Körpern, die sich durch starke analgetisch Eigenschaften auszeichnen. Die neuen Produkte besitzen eine gelbe Farbe, sind in Wasser, besonders beim Erwärmen, sowie in Alkohol, Äther und Azeton löslich.
Zweckmässig geschieht das Zusammenschmelzen im Verhältnis von 2 Molekülen des Pyrazolonderivates zu 1 Molekül der andern Komponente und bei Temperaturen, die etwa 1250 nicht Übersteigen.
Beispiel 1 : 5 Teile Dipropylbarbitursäure werden mit 12'5 Teilen 4-Dimethylamino-2, 3-dimethyl- - l-phenyl-5-pyrazolon unter Umrühren auf 1000 erhitzt, bis alles klar zu einer gelben Flüssigkeit geschmolzen ist. Die geschmolzene Masse wird heiss abgesaugt. Nach dem Erstarren werden die gelben Kristalle, die bei 82- 86 0 schmelzen, zur Trockne gebracht.
Beispiel 2 : 4'6 Teile Phenyläthylbarbitursäure werden bei einer Temperatur bis zu 1250 mit 9'2 Teilen 4-Dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolon, wie oben, zusammengeschmolzen und ebenso weiter behandelt. Die Verbindung schmilzt ganz allmählich zwischen 106-120 .
Beispiel 3 : Man erhitzt 2'08 Teile Diallylbarbitursäure mit 4"6 Teilen 4-Dimethylamino-2, 3-dimethyl-l-phenyl-5-pyrazolon unter Umrühren auf etwa 115 , bis alles zu einer gelben Flüssigkeit geschmolzen ist und verfährt dann weiter wie in den vorstehenden Beispielen. Die Verbindung schmilzt bei etwa 85-88 .
PATENT-ANSPRÜCHE :
1. Weitere Ausgestaltung des Verfahrens des Stammpatentes Nr. 89936 zum Zwecke der Darstellung von Verbindungen des 4-Dimethylamino-2, 3-dimethyl-1-phenyl-5-pyrazolons, dadurch gekennzeichnet, dass man dieses Pyrazolonderivat hier mit Homologen der Diäthylbarbitursäure zusammenschmilzt.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of compounds of 4, -Dimethylamino-2, 3-dimethyl- - 1-phenil-5-pyrazolone.
The parent patent no. 89936 relates to a process for preparing a compound of 4-dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone and diethylbarbituric acid, which consists in melting the two components together.
If, according to the present invention, one starts with homologues of diethylbarbituric acid, such as dipropyl-, diallyl-, phenylethylbarbituric acid, and treats them in the same way with 4-dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone, one also arrives at to bodies that are characterized by strong analgesic properties. The new products have a yellow color and are soluble in water, especially when heated, as well as in alcohol, ether and acetone.
It is practical if the fusion takes place in a ratio of 2 molecules of the pyrazolone derivative to 1 molecule of the other component and at temperatures not exceeding about 1250.
Example 1: 5 parts of dipropylbarbituric acid are heated with 12.5 parts of 4-dimethylamino-2,3-dimethyl- - 1-phenyl-5-pyrazolone to 1000 with stirring until everything has melted to a clear yellow liquid. The melted mass is sucked off hot. After solidification, the yellow crystals, which melt at 82-860, are brought to dryness.
Example 2: 4'6 parts of phenylethylbarbituric acid are melted together at a temperature of up to 1250 with 9'2 parts of 4-dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone, as above, and are also treated further. The compound melts very gradually between 106-120.
Example 3: 208 parts of diallyl barbituric acid are heated with 4 "6 parts of 4-dimethylamino-2,3-dimethyl-1-phenyl-5-pyrazolone to about 115 with stirring until everything has melted to a yellow liquid and then the process continues as in the previous examples, the compound melts at about 85-88.
PATENT CLAIMS:
1. Further embodiment of the process of the parent patent no. 89936 for the purpose of preparing compounds of 4-dimethylamino-2, 3-dimethyl-1-phenyl-5-pyrazolones, characterized in that this pyrazolone derivative is melted here with homologues of diethylbarbituric acid.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE89936X | 1920-01-26 | ||
| DE99014X | 1922-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT99014B true AT99014B (en) | 1925-01-10 |
Family
ID=25749967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT99014D AT99014B (en) | 1920-01-26 | 1923-05-12 | Process for the preparation of compounds of 4-dimethylamino-2,3-dimethyl-1-phenil-5-pyrazolone. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT99014B (en) |
-
1923
- 1923-05-12 AT AT99014D patent/AT99014B/en active
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