AT27417B - Process for the preparation of C -C dialkylbarbituric acids. - Google Patents
Process for the preparation of C -C dialkylbarbituric acids.Info
- Publication number
- AT27417B AT27417B AT27417DA AT27417B AT 27417 B AT27417 B AT 27417B AT 27417D A AT27417D A AT 27417DA AT 27417 B AT27417 B AT 27417B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- parts
- acids
- dialkylbarbituric acids
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 3
- 238000000034 method Methods 0.000 title claims description 3
- 150000007513 acids Chemical class 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 3
- 150000003230 pyrimidines Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- DPHBCBNBDNTWKL-UHFFFAOYSA-N 2,2-diethyl-3-hydroxybutanedinitrile Chemical compound C(C)C(C(C#N)O)(C#N)CC DPHBCBNBDNTWKL-UHFFFAOYSA-N 0.000 description 1
- UZRGQIZTJOPZGE-UHFFFAOYSA-N 2-cyano-2-propylpentanoic acid Chemical compound CCCC(C(O)=O)(C#N)CCC UZRGQIZTJOPZGE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- -1 diethyldiiminocyaniminopyrimidine Chemical compound 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- RCOUWKSZRXJXLA-UHFFFAOYSA-N propylbarbital Chemical compound CCCC1(CCC)C(=O)NC(=O)NC1=O RCOUWKSZRXJXLA-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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Beispiel 3 : 20 Teile des durch Kondensation von Diäthylmalonitril und Dicyan- diamid in Gegenwart von Alkalialkoholat erhältlichen Diäthyldiiminocyaniminopyrimidins vom Schmelzpunkt- 2700 werden mit 30 Teilen 40prozentiger Schwefelsäure 3 Stunden auf 110 erhitzt. Die Diäthytbarbitarsäure scheidet sich hiebei in einer Ausbeute von über 90% der Theorie ab. Sie wird darauf durch Umkristallisieren aus Wasser gereinigt.
Beispiel 4 : 10 Teile der durch Kondensation von Dipropylcyanessigester und Dicyandiamid in Gegenwart eines alkalischen Kondensationsmittels erhaltenen Dipropyliminocyaniminooxypyrimidins vom Schmelzpunkt 272 werden mit 30 Teilen 25prozentiger Bromwasserstoffsäure 4 Stunden auf 1200 erhitzt. Die Dipropylbarbitursäure scheidet sich beim Erkalten in einer Ausbeute von über 90% der Theorie ab und wird darauf durch Umkristallisieren aus Wasser gereinigt.
Beispiel 5 : 20 Teile des in Beispiel 1 erwähnten Cyaniminopyrimidins werden mit 30 Teilen Oxalsäure und 100 Teilen Wasser 5 Stunden am Rückflusskühler gekocht.
Nach dem Erkalten wird die gebildete Diäthylbarbitursäure, die in einer Ausbeute von über 900/0 der Theorie entstanden ist, abfiltriert und aus Wasser umkristallisiert.
In analoger Weise verfährt man bei Verwendung der ganz analog konstruierten, aus anderen Dialkylcyanessigestern, dialkylierten Malonestern bezw. Ma ! onitri ! en erhältlichen
Pyrimidinderivate.
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Example 3: 20 parts of the diethyldiiminocyaniminopyrimidine, obtainable by condensation of diethyl malonitrile and dicyandiamide in the presence of alkali metal alcoholate, with a melting point of 2700 are heated to 110 for 3 hours with 30 parts of 40 percent sulfuric acid. The dietary barbitaric acid separates out in a yield of over 90% of theory. It is then purified by recrystallization from water.
Example 4: 10 parts of the dipropyliminocyaniminooxypyrimidine, obtained by condensation of dipropylcyanoacetate and dicyandiamide in the presence of an alkaline condensing agent, with a melting point of 272, are heated to 1200 with 30 parts of 25 percent strength hydrobromic acid for 4 hours. The dipropylbarbituric acid separates out on cooling in a yield of over 90% of theory and is then purified by recrystallization from water.
Example 5: 20 parts of the cyaniminopyrimidine mentioned in Example 1 are refluxed with 30 parts of oxalic acid and 100 parts of water for 5 hours.
After cooling, the diethylbarbituric acid formed, which has a yield of over 900/0 of theory, is filtered off and recrystallized from water.
An analogous procedure is followed when using the completely analogously constructed, respectively, from other dialkylcyanoacetic esters, dialkylated malonic esters. Ma! onitri! en available
Pyrimidine derivatives.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE165223D | 1904-03-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT27417B true AT27417B (en) | 1907-02-11 |
Family
ID=5684974
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT27417D AT27417B (en) | 1904-03-18 | 1905-04-05 | Process for the preparation of C -C dialkylbarbituric acids. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT27417B (en) |
-
1905
- 1905-04-05 AT AT27417D patent/AT27417B/en active
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