CH93435A - Process for the preparation of a halogen-substituted barbituric acid derivative. - Google Patents
Process for the preparation of a halogen-substituted barbituric acid derivative.Info
- Publication number
- CH93435A CH93435A CH93435DA CH93435A CH 93435 A CH93435 A CH 93435A CH 93435D A CH93435D A CH 93435DA CH 93435 A CH93435 A CH 93435A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- barbituric acid
- halogen
- preparation
- acid derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 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 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 150000007656 barbituric acids Chemical class 0.000 claims description 4
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 4
- FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960000880 allobarbital Drugs 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- FSCNUJMKSQHQSY-UHFFFAOYSA-N Gein Chemical compound COC1=CC(CC=C)=CC=C1OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)CO2)O)O1 FSCNUJMKSQHQSY-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical group O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines halogensubstituierten BarbitursiLurederivates. plan hat sich schon vielfach bemüht, in Barbitursäurederivate Halogene, spei. Brom einzuführen, um die Wirkung dieser Arznei mittel zu erhöhen; bei bisherigen Versuchen hat man das Halogen in Seitenketten am Stickstoffatom eingeführt.
Es wurde nun gefunden, dass man in glatter Weise zu einem halogensubstituierten Derivat der Barbitursäure gelangen kann, wenn man Diallylbarbitursiture mit Bromwasserstoff, zweckmässig in Gegenwart von Verdünnungs mitteln, behandelt.
Der Barbitursäurekern wird hierbei nicht angegriffen und der Bromwasserstoff lagert sich glatt an die Doppelbindung der Seiten kette an unter Bildung einer @-j3-Dibroiii-di- propylbarbitursäure.
Dieselbe stellt ein weisses mikrokristal linisches Pulver vom Snip. 237-239o dar, welches in Äther, Alkohol, Aceton und Chloro form, sowie Eisessig löslich, in Wasser und verdünnter Essigsäure fast unlöslich ist.
Die neue Verbindung soll zu therapeu tischen Zwecken, sowie als Ausgangsmaterial zur Herstellung weiterer Barbitursäurederivate verwendet werden. <I>Beispiel:</I> 156 g Diallylbarbitursäure werden mit (i00 g einer<B><U>95</U></B> /oigen Bromwasserstoff eisessig- lösung in geschlossenem Uefüss auf 90--100" erhitzt; dabei ist zu beachten, dass bei Be ginn des Erwärmens die Diallylbarbitursäure sich vollständig löst.
Schon nach zweistün digem Erhitzen beginnt das Reaktionsprodukt auszukristallisieren, nach 10 Stunden ist der ganze Inhalt des Reaktionsgefässes zu einer festen Masse erstarrt. 17111 die Reaktion zu Ende zu führen; wird noch einen Tag weiter erhitzt. Das Rohprodukt wird auf der -Nutsche mit heit)ein Wasser gewaschen und kann zum Meinigen ans Alkohol umkristallisiert werden.
Process for the preparation of a halogen-substituted barbituric acid derivative. plan has already tried many times to save halogens in barbituric acid derivatives. Introduce bromine to increase the effectiveness of these drugs; in previous attempts the halogen has been introduced in side chains on the nitrogen atom.
It has now been found that a halogen-substituted derivative of barbituric acid can be obtained in a smooth manner if diallyl barbiturates are treated with hydrogen bromide, expediently in the presence of diluents.
The barbituric acid core is not attacked and the hydrogen bromide is deposited smoothly on the double bond of the side chain, forming a @ -j3-dibroiii-propylbarbituric acid.
It represents a white microcrystalline line powder from the snip. 237-239o, which is soluble in ether, alcohol, acetone and chloro form, as well as glacial acetic acid, and is almost insoluble in water and dilute acetic acid.
The new compound is to be used for therapeutic purposes and as a starting material for the production of other barbituric acid derivatives. <I> Example: </I> 156 g of diallyl barbituric acid are heated with (100 g of a <B> <U> 95 </U> </B> / o hydrogen bromide glacial acetic acid solution in a closed vessel to 90-100 "; It should be noted that the diallylbarbituric acid dissolves completely at the start of heating.
After just two hours of heating, the reaction product begins to crystallize, and after 10 hours the entire contents of the reaction vessel have solidified into a solid mass. 17111 to complete the reaction; is heated for another day. The crude product is washed on the suction filter with water and can be recrystallized from alcohol to remove it.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH93435T | 1921-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH93435A true CH93435A (en) | 1922-03-01 |
Family
ID=4350973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH93435D CH93435A (en) | 1921-01-25 | 1921-01-25 | Process for the preparation of a halogen-substituted barbituric acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH93435A (en) |
-
1921
- 1921-01-25 CH CH93435D patent/CH93435A/en unknown
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