AT21677B - Process for the preparation of the C -C dialkyliminobarbituric acids. - Google Patents
Process for the preparation of the C -C dialkyliminobarbituric acids.Info
- Publication number
- AT21677B AT21677B AT21677DA AT21677B AT 21677 B AT21677 B AT 21677B AT 21677D A AT21677D A AT 21677DA AT 21677 B AT21677 B AT 21677B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- acids
- dialkyliminobarbituric
- parts
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000007513 acids Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VYNDVGQITVIIAE-UHFFFAOYSA-N 2-benzyl-2-cyano-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1CC(C#N)(C(=O)O)CC1=CC=CC=C1 VYNDVGQITVIIAE-UHFFFAOYSA-N 0.000 description 1
- JSVFGUVEXOEQEC-UHFFFAOYSA-N 5-imino-1,3-diazinane-2,4,6-trione Chemical class N=C1C(=O)NC(=O)NC1=O JSVFGUVEXOEQEC-UHFFFAOYSA-N 0.000 description 1
- -1 Dibenzoyl iminobarbituric acid Chemical compound 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Verfahren zur Darstellung der C-C-Dialkyliminobarbitursäuren.
EMI1.1
Produkte leicht aus Dialkyicyanessigestern und Harnstoff durch Einwirkung von Metallalkoholaten hergestellt werden können nach folgender Gleichung :
EMI1.2
Diese Iminobarbitursäuren haben die Eigenschaft, sich leicht durch Ammoniak abspaltende Mittel in die entsprechenden Barbitursäuron verwandeln zu lassen. Sie bilden daher ein sehr wichtiges Zwischenglied in dem Verfahren zur Darstellung der therapeutisch so wichtigen Dialkylbarbitursäuren aus Dialkylcyanessigsäuresstern und Harnstoff. Sie sollen
EMI1.3
Beispiel 1.
Diäthyliminobarbitursäure. 23 oder besser 46 Teile Natrium werden in möglichst wenig absolutem Alkohol gelost ; nach dem Abkühlen werden 1 G ! I Teile Diäthylcyanessigsäureät4hylester und 60 bis 70 Teile gepulverter Harnstoff hinzugefügt und das Gemisch im Wasserbade erhitzt. Nach zwei bis drei Stunden verdunstet man den Alkohol und neutralisiert den Rückstand mit der auf die angewandte Menge Natrium berechneten Menge verdünnter Kssigsäurc bezw. auch Salzsäure oder Schwefelsäure. Die hiebei ausgeschiedene Substanz wird nun mit verdünnter Salzlsäure in der kalte digeriert
EMI1.4
70 Teile Harnstoff werden in die alkoholische Lösung von 23 oder bosser 4 (i Teilen Natrium eingetragen und das Gemisch auf dem Wasserbade erhitzt.
Nach etwa zwei Stunden verdunstet man den Alkohol und neutralisiert mit der auf das Natrium berechneten Menge
EMI1.5
in verdünnter Salzsäure in der Kälte auf und fällt dann wieder mit Ammoniak, so ist das Präparat genügend rein. Es schmilzt unter Zersetzung bei 3050.
Beispiel 3. Dibenzyliminobarbitursäure. Dibenzyliminobarbitursäure wird ebenso wie die vorhergehende Substanz dargestellt. Man gebraucht auf 23 oder besser 46 Teile Natrium und 70 Teile Harnstoff 293 Teile Dibenzylcyanessigester. Die Dibenzoyl- iminobarbitursäure ist in heissem Wasser sehr wenig löslich ; sie kann aus siedendem Alkohol umkristallisiert worden.
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EMI2.1
<Desc / Clms Page number 1>
Process for the preparation of the C -C dialkyliminobarbituric acids.
EMI1.1
Products easily made from dialkyicyaneacetic esters and urea through the action of metal alcoholates can be made according to the following equation:
EMI1.2
These iminobarbituric acids have the property of being easily converted into the corresponding barbituric acid by ammonia-releasing agents. They therefore form a very important link in the process for the preparation of the therapeutically important dialkylbarbituric acids from dialkylcyaneacetic acid star and urea. You should
EMI1.3
Example 1.
Diethyliminobarbituric acid. 23 or better 46 parts of sodium are dissolved in as little absolute alcohol as possible; after cooling, 1 G! I parts of ethyl cyanoacetate and 60 to 70 parts of powdered urea were added and the mixture was heated in a water bath. After two to three hours, the alcohol is evaporated and the residue is neutralized with the amount of dilute Kssigsäurc calculated on the amount of sodium used. also hydrochloric acid or sulfuric acid. The substance separated out is now digested in the cold with dilute hydrochloric acid
EMI1.4
70 parts of urea are added to the alcoholic solution of 23 or 4 parts sodium and the mixture is heated on a water bath.
After about two hours, the alcohol is evaporated and neutralized with the amount calculated for the sodium
EMI1.5
in dilute hydrochloric acid in the cold and then falls again with ammonia, the preparation is sufficiently pure. It melts with decomposition at 3050.
Example 3. Dibenzyliminobarbituric acid. Dibenzyliminobarbituric acid is represented as well as the preceding substance. For 23 or better 46 parts of sodium and 70 parts of urea, 293 parts of dibenzylcyanoacetate are used. Dibenzoyl iminobarbituric acid is very sparingly soluble in hot water; it can be recrystallized from boiling alcohol.
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EMI2.1
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1903156384D DE156384C (en) | 1903-07-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT21677B true AT21677B (en) | 1905-10-10 |
Family
ID=5677777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT21677D AT21677B (en) | 1903-07-11 | 1904-10-31 | Process for the preparation of the C -C dialkyliminobarbituric acids. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT21677B (en) |
-
1904
- 1904-10-31 AT AT21677D patent/AT21677B/en active
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