CH280321A - Process for producing a spiro-thiobarbituric acid compound. - Google Patents
Process for producing a spiro-thiobarbituric acid compound.Info
- Publication number
- CH280321A CH280321A CH280321DA CH280321A CH 280321 A CH280321 A CH 280321A CH 280321D A CH280321D A CH 280321DA CH 280321 A CH280321 A CH 280321A
- Authority
- CH
- Switzerland
- Prior art keywords
- spiro
- thiobarbituric acid
- producing
- acid compound
- diethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- -1 2,5-diethylcyclopentane-1,1-dicarboxylic acid ester Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- RUUVWUNHERVOAY-UHFFFAOYSA-N 1,3-diethylcyclopentane Chemical compound CCC1CCC(CC)C1 RUUVWUNHERVOAY-UHFFFAOYSA-N 0.000 description 1
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung einer Spiro-thiobarbitursäureverbindung. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung einer neuen Spiro-thiobarbitursäureverbindung, nämlich der Spiro-2,5-diäthyl-eyclopentan-(1),5'-thio- barbitursäure.
Die neue Verbindung besitzt geringe Toxi- zität und weist wertvolle sedative und ein schläfernde Eigenschaften auf, wobei sie in kleinen Dosen wirksam ist und schon nach kurzer Zeit Anästhesie hervorruft. Das Verfahren des vorliegenden Patentes zur Herstellung der Verbindung ist dadurch gekennzeichnet, dass man einen 2,5-Diäthyl- cyclopentan-1,1-dicarbonsäiireester mit Thio- harnstoff kondensiert. Das erfindungsgemässe Verfahren kann durch die folgenden Formeln veranschaulicht werden, worin -0E einen Al koholrest, z. B. den Rest eines niedrigen Alko hols, bedeutet. .
EMI0001.0013
Die neue Barbitursäure kann in Salze über geführt werden. So kann zum Beispiel das Kaliumsalz durch Umsetzung der Säure mit Kaliumalkoholat in wasserfreier Alkohollösung oder mittels Kaliumhydroxyd in wässeriger Alkohollösung, hergestellt werden. Durch Ver dampfen der Lösung des Salzes erhält man das trockene Salz.
Zu pharmazeutischen Zwecken wird ein lösliches Salz, z. B. das Natriumsalz, bevorzugt. Die neue Verbindung besitzt eine verhältnis mässig niedrige Wasserlöslichkeit. Wenn auch die saure Form sieh zur oralen und paren- teralen Verabreichung eignet, wird man trotz dem ein wasserlösliches Material vorziehen, weshalb man die Verbindung vorzugsweise in Form ihrer wasserlöslichen Salze anwenden wird.
<I>Beispiel:</I> 48 g 1,1-Dicarbäthoxy-2,5-diäthyl-cyclopen- tan werden in eine Lösung von 12,4 g Natrium in 160 em3 absolutem Methanol eingetragen. Man versetzt die Lösung mit 20,5 g Thioharn- stoff und lässt das Gemisch während etwa 7 Stunden unter Rückfluss sieden.
Man ver treibt das Methanol durch Eindampfen und löst den Rückstand, welcher die Spiro 2,5-di- äthyl-eyclopentan- (1),5'-thiobarbitursäure in Form ihres Natriumsalzes enthält, in Wasser. Man extrahiert die wässerige Lösung mehrere Male mit Äther, um alkaliunlösliehes Material zu entfernen, und verwirft die Ätherextrakte. Die Lösung wird mit verdünnter Salzsäure angesäuert, worauf die Spiro-2,5-diäthyl-eyclo- pentan-(1),5'-thiobarbitursäure ausfällt.
Die Thiobarbitursäure wird abfiltriert, mit Was ser gewaschen und durch wiederholtes Umkri- stallisieren aus Benzol gereinigt.
Die so erhaltene Spixo-2,5-diäthyl-cyclo- pentan- (1),5'-thiobarbitursäure schmilzt bei etwa 162 bis 164 C. Die Analyse ergab einen Stickstoffgehalt von 11,02%, während der be- rechnete Stickstoffgehalt. 11,04% beträgt.
Process for producing a spiro-thiobarbituric acid compound. The present invention relates to a process for the production of a new spiro-thiobarbituric acid compound, namely spiro-2,5-diethyl-eyclopentan (1), 5'-thiobarbituric acid.
The new compound is low in toxicity and has valuable sedative and sleep-inducing properties, being effective in small doses and causing anesthesia after a short time. The process of the present patent for the preparation of the compound is characterized in that a 2,5-diethylcyclopentane-1,1-dicarboxylic acid ester is condensed with thiourea. The inventive method can be illustrated by the following formulas, wherein -0E is an alcohol radical, for. B. the remainder of a low alcohol means. .
EMI0001.0013
The new barbituric acid can be converted into salts. For example, the potassium salt can be prepared by reacting the acid with potassium alcoholate in anhydrous alcohol solution or by means of potassium hydroxide in an aqueous alcohol solution. The dry salt is obtained by evaporating the solution of the salt.
For pharmaceutical purposes a soluble salt, e.g. B. the sodium salt is preferred. The new compound has a relatively low solubility in water. Even if the acidic form is suitable for oral and parenteral administration, a water-soluble material will nevertheless be preferred, which is why the compound is preferably used in the form of its water-soluble salts.
<I> Example: </I> 48 g 1,1-dicarbethoxy-2,5-diethyl-cyclopentane are introduced into a solution of 12.4 g sodium in 160 cubic meters of absolute methanol. The solution is mixed with 20.5 g of thiourea and the mixture is allowed to reflux for about 7 hours.
The methanol is driven off by evaporation and the residue, which contains the spiro 2,5-diethyl-cyclopentane (1), 5'-thiobarbituric acid in the form of its sodium salt, is dissolved in water. The aqueous solution is extracted several times with ether in order to remove alkali-insoluble material, and the ether extracts are discarded. The solution is acidified with dilute hydrochloric acid, whereupon the spiro-2,5-diethyl-cyclopentane (1), 5'-thiobarbituric acid precipitates.
The thiobarbituric acid is filtered off, washed with water and purified by repeated recrystallization from benzene.
The spixo-2,5-diethyl-cyclopentane (1), 5'-thiobarbituric acid thus obtained melts at about 162 to 164 ° C. The analysis showed a nitrogen content of 11.02%, while the calculated nitrogen content. 11.04%.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US280321XA | 1949-03-19 | 1949-03-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH280321A true CH280321A (en) | 1952-01-15 |
Family
ID=21841179
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH280321D CH280321A (en) | 1949-03-19 | 1949-06-14 | Process for producing a spiro-thiobarbituric acid compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH280321A (en) |
-
1949
- 1949-06-14 CH CH280321D patent/CH280321A/en unknown
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