CH116524A - Process for the preparation of a derivative of barbituric acid. - Google Patents
Process for the preparation of a derivative of barbituric acid.Info
- Publication number
- CH116524A CH116524A CH116524DA CH116524A CH 116524 A CH116524 A CH 116524A CH 116524D A CH116524D A CH 116524DA CH 116524 A CH116524 A CH 116524A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- acid
- derivative
- barbituric acid
- isopropylbarbituric
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000007656 barbituric acids Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 5
- GFPIGNBQTXNNAG-UHFFFAOYSA-N 5-propan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound CC(C)C1C(=O)NC(=O)NC1=O GFPIGNBQTXNNAG-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- MAYPXMSOHAQNPB-UHFFFAOYSA-N 3-bromo-2-chloroprop-1-ene Chemical compound ClC(=C)CBr MAYPXMSOHAQNPB-UHFFFAOYSA-N 0.000 description 2
- AONKGGMHQHWMSM-UHFFFAOYSA-N 1,1,1-tribromopropane Chemical compound CCC(Br)(Br)Br AONKGGMHQHWMSM-UHFFFAOYSA-N 0.000 description 1
- -1 1,2-dichloro-2,3-propylene Chemical group 0.000 description 1
- DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical class FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
Description
Verfahren zur Darstellung eines Derivate, der Barbitur,äure. Im. Hauptpatent wurde gezeigt, dass solche an der Methylengruppe substituierte Barbitursäuren, bei welchen mindestens ein Methylenwasserstoffatom durch einen ss-Bro- mallylrest ersetzt ist, ausgezeichnet wirk same Schlafmittel vorstellen.
In weiterer Entwicklung des Verfahrens des Haupt patentes wurde gefunden, dass überraschen derweise der ss-Chlorallylrest die Wirksam keit der Barbitursäuren ebenfalls äusserst günstig beeinflusst.
Die Darstellung der neuen Verbindung geschieht analog dem im Hauptpatent be schriebenen Verfahren, indem man an Stelle des 1.2-Dibrom-2.3-propylens bezw. des Tribrompropans 1 Halogen-2-Chlor-2. 3-pro- pylen von der Formel CH- (Hlg)-CCl = CHZ (wobei Hlg Chlor oder Brom bedeutet) auf Isopropylbarbitursäure zur Einwirkung bringt.
<I>Beispiel</I> 170 Gewichtsteile Isopropylbarbitursäure werden in 500 Volumenteilen zweifach nor mal Natronlauge gelöst und nach Zusatz von 125 Gewichtsteilen 1.2-Dichlor-2.3-pro- pylen mehrere Stunden bei lebhaftem Rühren unter Rückfluss erwärmt. Nach beendeter Einwirkung wird das ausgeschiedene Reak tionsprodukt abgesaugt und aus wässerigem Alkohol umkristallisiert. Es wird in langen farblosen, filzigen Nadeln vom Fp. <B>171</B> er halten und stellt, wie die Anlayse ergibt, die ss-Monochlorallyl-isopropylbarbitursäure vor.
Dieses Barbitursäurederivat ist in Alko hol, Äther und Aceton leicht löslich, in Chloroform, Tetralin und Wasser schwer löslich. Es wird von verdünnter Sodalösung und Natronlauge leicht aufgenommen und mit Säuren aus seiner alkalischen Lösung un verändert abgeschieden.
Zum gleichen Produkt kommt man, wenn 2-Chlor-3-brompropen-(1) unter denselben Reaktionsbedingungen auf das Natriumsalz der Isopropylbarbitursäure einwirken lässt.
Process for the preparation of a derivative, the barbituric acid. In the main patent it was shown that those barbituric acids substituted on the methylene group, in which at least one methylene hydrogen atom has been replaced by an β-bromallyl radical, present excellently effective sleeping pills.
In a further development of the process of the main patent, it was found that, surprisingly, the ß-chlorallyl radical also has an extremely beneficial effect on the effectiveness of the barbituric acids.
The presentation of the new compound is done analogously to the process described in the main patent by BEZW instead of 1.2-dibromo-2.3-propylene. of tribromopropane 1 halogen-2-chloro-2. 3-propylene of the formula CH- (Hlg) -CCl = CHZ (where Hlg denotes chlorine or bromine) acts on isopropylbarbituric acid.
<I> Example </I> 170 parts by weight of isopropylbarbituric acid are dissolved twice normal sodium hydroxide solution in 500 parts by volume and, after addition of 125 parts by weight of 1,2-dichloro-2,3-propylene, heated under reflux for several hours with vigorous stirring. After the action has ended, the precipitated reaction product is filtered off with suction and recrystallized from aqueous alcohol. It is obtained in long, colorless, felt-like needles with a melting point of <B> 171 </B> and, as the analysis shows, it represents ß-monochloroallyl-isopropylbarbituric acid.
This barbituric acid derivative is easily soluble in alcohol, ether and acetone, and sparingly soluble in chloroform, tetralin and water. It is easily absorbed by dilute soda solution and sodium hydroxide solution and separated from its alkaline solution with acids without any changes.
The same product is obtained if 2-chloro-3-bromopropene (1) is allowed to act on the sodium salt of isopropylbarbituric acid under the same reaction conditions.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH116524T | 1924-09-19 | ||
| CH111883T | 1924-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH116524A true CH116524A (en) | 1926-09-01 |
Family
ID=25707949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH116524D CH116524A (en) | 1924-09-19 | 1924-09-19 | Process for the preparation of a derivative of barbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH116524A (en) |
-
1924
- 1924-09-19 CH CH116524D patent/CH116524A/en unknown
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