CH181733A - Process for the preparation of a compound of 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone with B-bromoallyl-isopropylbarbituric acid. - Google Patents
Process for the preparation of a compound of 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone with B-bromoallyl-isopropylbarbituric acid.Info
- Publication number
- CH181733A CH181733A CH181733DA CH181733A CH 181733 A CH181733 A CH 181733A CH 181733D A CH181733D A CH 181733DA CH 181733 A CH181733 A CH 181733A
- Authority
- CH
- Switzerland
- Prior art keywords
- isopropyl
- phenyl
- pyrazolone
- dimethyl
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 10
- PXWLVJLKJGVOKE-UHFFFAOYSA-N propyphenazone Chemical compound O=C1C(C(C)C)=C(C)N(C)N1C1=CC=CC=C1 PXWLVJLKJGVOKE-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 230000000202 analgesic effect Effects 0.000 claims description 2
- 230000001754 anti-pyretic effect Effects 0.000 claims description 2
- 239000002221 antipyretic Substances 0.000 claims description 2
- 229960003153 aprobarbital Drugs 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- -1 arylalkyl barbituric acids Chemical class 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung einer Verbindung des 1-Plienyl-2,3-diinethyl- 4-isopropyl-5-pyrazolons mit ss-Bromallyl-isopropylbarbitursäure. Es ist bekannt, dass sowohl 1-Phenyl-2,3- dimetliyl-:)-pyrazolon, als auch 1-Phenyl- :
), 3 - (1i me thy 1- 4 - dimethy lamino - 5- pyrazolon ,ich mit Dialkyl- und Arylalkylbarbitur- sä.uren verbinden (PatentschriftenNr.l20098. 120444,46, 121981/85 und 9<B>1751,</B> 113103/05, <B>113056,</B> 113295/97). Entsprechende Verbin dungen mit 4-- Alkylpyrazolonen sind bis ,jetzt noch nicht hergestellt worden.
'Wie nun gefunden wurde, verhält sich das 1-Phenyl-2, 3-dimethyl-4-isopropyl-5-pyr- azolon nicht gleich wie das 1-Phenyl-9,3-di- itietliyl-5-pyrazolon und das 1-Phenyl-?,3-di- methyl.-42 dimethylamino.5-pyrazolon. Es geht nämlich nur mit solchen C,C-disubsti- tnierten Barbitursäuren Verbindungen ein, die nur gesättigte oder höchstens nur einen ungesättigten Nlubstituenten besitzen.
Sind beide Substituenten ungesättigt, so unter bleibt die Bildung von Verbindungen.
Die Darstellung der neuen Verbindungen gestaltet sich bei. der grossen Neigung der Ausgangsstoffe zum Zusammentritt sehr ein fach. Man schmilzt das 1-Phenyl-2,3-di- methyl-4-isopropyl-5-pyrazolon mit der äqui- molekularen Menge einer Dialkyl- oder Arylalkylbarbitursäure zusammen oder lässt die Ausgangsstoffe in Gegenwart eines Lö- sungs- bezw. Verdiinnungsmittels aufeinan der einwirken. Die Vereinigung des 1- Phenyl
-<B>2.3</B> - dimethyl -4 -isopropyl - 5 -pyrazo- lons mit den Dialkyl- bezw. Arylalkylbar- bitursäuren erfolgt stets im molekularen Verhältnis auch dann, wenn von dem einen oder andern Bestandteil wesentlich grössere Mengen, zum Beispiel 2 Moleküle, vorhanden sind.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung einer Verbin dung des 1-Phenyl-2,3-dimethyl-4-isopropyl- 5-pyrazolons mit ss-Bromallyl-isopropyl-bar- bitursäure, welches dadurch gekennzeichnet ist, dass man 1-Phenyl-2,3-dimethyl-4-isopro- pyl-5-pyrazolon und ss-Bromallyl-isopropyl- barbitursäure im Molekularverhältnis 1 :1 aufeinander einwirken lässt. Die. Ausgangs stoffe können zum Beispiel in geschmolze nem Zustand oder in einem Lösungsmittel aufeinander einwirken gelassen werden.
Die Verbindung des 1-Phenyl 2-,3-di- methyl-4-isopropyl-5-pyrazolons mit ss-Brom- allyl-isopropyl-barbitursäure kristallisiert in feinen, farblosen Nadeln, die bei 134 bis 135 schmelzen. Sie lässt sich durch Behan deln mit Lösungsmitteln nicht in die Be standteile zerlegen. In organischen Lösungs mitteln ist sie leicht, in Wasser schwer lös lich. Sie soll als Arzneimittel Verwendung finden, da sie sowohl analgetische bezw. antipyretische,_ als auch schlafmachende Wirkungen besitzt.
Beispiel: 290 Teile ss-Bromallyl-isopropyl-barbi- tursäLire werden in 900 Teilen 90%igem Alkohol gelöst. Dann wird eine Lösung von 230 Teilen 1-Phenyl-2,3-dimethyl-4-isopro- pyl-5-pyrazolon in 500 Teilen 90 % igeln Alkohol hergestellt. Die beiden Lösungen werden warm zusammengegossen. Aus der klaren, farblosen Mischung fallen beim Ab kühlen 480 Teile der neuen Verbindung aus. Die farblosen Nadeln schmelzen bei 134 bis 135 .
Durch Zufügen von wenig Wasser zu der Mutterlauge können weitere 30 Teile ge wonnen werden, welche nach einmaligem Umkristallisieren aus verdünntem Alkohol ebenfalls den Schmelzpunkt von 13-1 bis 135 aufweisen.
Process for the preparation of a compound of 1-plienyl-2,3-diinethyl-4-isopropyl-5-pyrazolone with s-bromoallyl-isopropylbarbituric acid. It is known that 1-phenyl-2,3-dimetliyl -:) - pyrazolon, and 1-phenyl-:
), 3 - (1i me thy 1- 4 - dimethy lamino - 5-pyrazolone, I combine with dialkyl and arylalkyl barbituric acids (patent specifications no.120098. 120444,46, 121981/85 and 9 <B> 1751, < / B> 113103/05, <B> 113056, </B> 113295/97). Corresponding compounds with 4- alkylpyrazolones have not yet been produced.
As has now been found, the 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone does not behave in the same way as the 1-phenyl-9,3-di-itietliyl-5-pyrazolone and the 1 -Phenyl- ?, 3-dimethyl.-42 dimethylamino.5-pyrazolone. This is because it only forms compounds with those C, C-disubstituted barbituric acids which have only saturated or at most only one unsaturated substituent.
If both substituents are unsaturated, compounds are not formed.
The representation of the new connections takes place at. the great tendency of the starting materials to come together very simply. The 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone is melted with the equimolar amount of a dialkyl or arylalkyl barbituric acid or the starting materials are left in the presence of a solution or. Thinners act on one another. The union of 1-phenyl
- <B> 2.3 </B> - dimethyl -4 -isopropyl - 5 -pyrazolons with the dialkyl or. Arylalkylbarbituric acids always take place in the molecular ratio, even if there are significantly larger amounts of one or the other component, for example 2 molecules.
The subject of the present patent is a process for the preparation of a compound of 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone with s-bromoallyl-isopropyl-barbituric acid, which is characterized in that 1- Phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone and ß-bromoallyl-isopropylbarbituric acid in a molecular ratio of 1: 1. The. Starting materials can, for example, be allowed to act on one another in a molten state or in a solvent.
The compound of 1-phenyl 2-, 3-dimethyl-4-isopropyl-5-pyrazolone with s-bromo-allyl-isopropylbarbituric acid crystallizes in fine, colorless needles that melt at 134-135. It cannot be broken down into its components by treating it with solvents. It is light in organic solvents and sparingly soluble in water. It should be used as a drug because it is both analgesic and. has antipyretic and sleep-inducing effects.
Example: 290 parts of ss-bromoallyl-isopropyl-barbitursäLire are dissolved in 900 parts of 90% alcohol. A solution of 230 parts of 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone in 500 parts of 90% alcohol is then prepared. The two solutions are poured together warm. From the clear, colorless mixture, 480 parts of the new compound precipitate on cooling. The colorless needles melt at 134 to 135.
By adding a little water to the mother liquor, a further 30 parts can be obtained, which, after recrystallizing once from dilute alcohol, also have a melting point of 13-1 to 135.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE181733X | 1934-01-08 | ||
| CH179887T | 1934-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH181733A true CH181733A (en) | 1935-12-31 |
Family
ID=25720348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH181733D CH181733A (en) | 1934-01-08 | 1934-11-20 | Process for the preparation of a compound of 1-phenyl-2,3-dimethyl-4-isopropyl-5-pyrazolone with B-bromoallyl-isopropylbarbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH181733A (en) |
-
1934
- 1934-11-20 CH CH181733D patent/CH181733A/en unknown
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