AT39445B - Process for the preparation of CC-dialkylated barbituric acids. - Google Patents
Process for the preparation of CC-dialkylated barbituric acids.Info
- Publication number
- AT39445B AT39445B AT39445DA AT39445B AT 39445 B AT39445 B AT 39445B AT 39445D A AT39445D A AT 39445DA AT 39445 B AT39445 B AT 39445B
- Authority
- AT
- Austria
- Prior art keywords
- dialkylated
- preparation
- acids
- barbituric acids
- barbituric
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000007656 barbituric acids Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000002826 nitrites Chemical class 0.000 claims description 3
- -1 diethyl compound Chemical class 0.000 claims 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von CC-dialkylierten Barbitursäuren.
In dem D. R. P. Nr. 189076 ist ein Verfahren zur Umwandlung der durch Kondensation von Dialkylmalonsäureestern mit Guanidin und folgende Alkylierung erhältlichen Dialkylmalonylguanidine (5-Dialkyl-2-imino-4.6-dioxypyrimidine) in CC-Dialkylbarbitursäuren durch Behandlung mit Nitriten in saurer Lösung beschrieben.
Es hat sich nun gezeigt, dass man diese Umwandlung auch ohne Zusatz von Nitriten durch blosse Behandlung, der Dialkylmalonylguanidine mit Säuren herbeiführen kann. Hierbei wird durch Hydrolyse an Stelle der Iminogruppe der Ausgangsmaterialien Sauerstoff eingeführt. Nur die dialkylierten Barbitursäuren lassen sich in dieser Weise darstellen, während bei den Monoverbindungen das Verfahren versagt.
EMI1.1
Nr. 189076 angegebenen Weis dargostellt wird, mit 10 kg rauchender Salzsäure 4 Stunden lang auf etwa 125 bis 1300, dem Erkalten wird das Reaktionsprodukt in Wasser eingetragen, wobei sich die C ('-L) iäthylbarbitursäure abscheidet. Durch Umkristallisieren aus Wasser wird die Verbindung weiter gereinigt.
B e i s p i e l 2: 5 kg Diathylmalonylguanidin werden mit 25 k ! " 10prozontiger Schwefelsäure 2 Stunden lang am Rückflusskühler erhitzt. Beim Erkalten kristallisiert die Diäthylbarbitursäure aus, die weiter gereinigt wird.
Beispiel 3 : 1 kg Diäthylmalonylguanidin wird mit 12 kg Bromwasserstoffsäure im geschlossenen Rohr mehrere Stunden lang erhitzt. Beim Erkalten scheidet sich das Roaktionsprodukt aus.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of CC-dialkylated barbituric acids.
In the D. R. P. No. 189076 a process for converting the dialkylmalonylguanidines (5-dialkyl-2-imino-4,6-dioxypyrimidines) obtainable by condensation of dialkylmalonic acid esters with guanidine and subsequent alkylation into CC-dialkylbarbituric acids by treatment with nitrites in acidic solution is described.
It has now been shown that this conversion can also be brought about without the addition of nitrites by simply treating the dialkylmalonylguanidines with acids. In this case, instead of the imino group of the starting materials, oxygen is introduced by hydrolysis. Only the dialkylated barbituric acids can be prepared in this way, while the process fails with the mono compounds.
EMI1.1
No. 189076 indicated Weis is dargostellt, with 10 kg of fuming hydrochloric acid for 4 hours to about 125 to 1300, cooling the reaction product is introduced into water, whereby the C ('-L) iäthylbarbituräure separates out. The compound is further purified by recrystallization from water.
Example 2: 5 kg of diethylmalonylguanidine are mixed with 25 k! "10% sulfuric acid heated on the reflux condenser for 2 hours. When it cools, the diethylbarbituric acid crystallizes out and is further purified.
Example 3: 1 kg of diethylmalonylguanidine is heated with 12 kg of hydrobromic acid in a closed tube for several hours. When cooling down, the raw material is separated out.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE201244D | 1903-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT39445B true AT39445B (en) | 1909-10-25 |
Family
ID=5765234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT39445D AT39445B (en) | 1903-10-07 | 1908-09-22 | Process for the preparation of CC-dialkylated barbituric acids. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT39445B (en) |
-
1908
- 1908-09-22 AT AT39445D patent/AT39445B/en active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3011391C2 (en) | ||
| AT39445B (en) | Process for the preparation of CC-dialkylated barbituric acids. | |
| DE2207184A1 (en) | METHOD FOR CLEANING UP ACRYLIC ACID | |
| DE1643275B2 (en) | Process for the preparation of 1,3-diaminopropanol- (2) | |
| AT87661B (en) | Process for the preparation of hydrogen peroxide by distillation. | |
| AT227268B (en) | Process for the preparation of the new 2-hydroxymethylpiperazine | |
| AT60761B (en) | Process for the preparation of β-γ-dimethylbutadiene. | |
| DE171835C (en) | ||
| DE730182C (en) | Process for the preparation of N- (aminoalkyl) pyrrolidones | |
| DE1277239C2 (en) | PROCESS FOR THE RECOVERY OF ADIPIC ACID FROM THE ACID WASHING WATERS OF CYCLOHEXANE AIR OXYDATION | |
| DE1236493B (en) | Process for the production of benzaldehyde | |
| AT45445B (en) | Process for the production of fatty acid anhydrides, especially acetic anhydride, from fatty acid salts. | |
| AT30313B (en) | Process for the preparation of CC dialkylbarbituric acids. | |
| DE3432575C2 (en) | ||
| AT35662B (en) | Process for the preparation of CC dialkylbarbituric acids. | |
| AT70875B (en) | Process for the production of betaine or betaine salts from molasses, molasses liquor or other processes in beet sugar production. | |
| AT69850B (en) | Process for the production of pure trinitrotoluene from crude trinitrotoluene. | |
| AT229276B (en) | Process for cleaning exhaust air from viscose factories | |
| AT87799B (en) | Process for the preparation of bromodialkylacetecarbamides. | |
| AT24749B (en) | Process for the preparation of C -C dialkylbarbituric acids. | |
| AT19001B (en) | Process for the production of m-cresol from raw cresol. | |
| DE545266C (en) | Process for the preparation of diiodochelidamic acid | |
| AT261568B (en) | Process for the production of ω-laurinolactam | |
| AT237591B (en) | Process for the preparation of the new 1-cyclohexyl-2-aminopropanone- (1) and its salts | |
| AT52846B (en) | Process for the preparation of bromine diethyl acetylurea. |