CH168366A - Process for the preparation of an N-alkylated derivative of barbituric acid. - Google Patents
Process for the preparation of an N-alkylated derivative of barbituric acid.Info
- Publication number
- CH168366A CH168366A CH168366DA CH168366A CH 168366 A CH168366 A CH 168366A CH 168366D A CH168366D A CH 168366DA CH 168366 A CH168366 A CH 168366A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- preparation
- barbituric acid
- cyclopentenyl
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 5
- 150000007656 barbituric acids Chemical class 0.000 title description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 235000019441 ethanol Nutrition 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 3
- 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 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 5
- -1 cyanoacetic acid ester Chemical class 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- AOKRXIIIYJGNNU-UHFFFAOYSA-N 3-methylcyclopentan-1-one Chemical compound CC1CCC(=O)C1 AOKRXIIIYJGNNU-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000006203 ethylation Effects 0.000 description 3
- 238000006200 ethylation reaction Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- MLIREBYILWEBDM-UHFFFAOYSA-N anhydrous cyanoacetic acid Natural products OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung eines N-alkylierten Abkömmlings der Barbitursäure. Das Hauptpatent betrifft ein Verfahren zur Darstellung einer N-alkylierten C-disub- stituierten Barbitursäure.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer C-Äthyl- C -(methyl -d-1.2 - cyclopentenyl) - N- methyl- barbitursäure. Das Verfahren ist dadurch ge kennzeichnet, dass man einen Äthyl-(methyl- d-1.2-cyclopentenyl)-cyanessigsäureester,
wie er erhältlich ist durch Kondensation von 3- Methyl-cyclopentanon mit Cyanessigsäureester und Äthylierung des dabei entstandenen (Methyl-d-1. 2-cyclopentenyl)-cyanessigsäure- esters mit Monomethylharnstoff in Gegenwart einreg Kondensationsmittels kondensiert und das entstandene Zwischenprodukt zur C-Me- thyl -C- (methyl-d-1. 2 - cyclopentenyl)
-N-me- thylbarbitursäure verseift.
Als Kondensationsmittel verwendet man zweckmässig Metallalkoholate, insbesondere solche der Alkalimetalle. Dabei ist es vorteil haft als Verdünnungsmittel einen Alkohol, z. B. Äthylalkohol, zuzusetzen. Die Verseifung geschieht vorteilhaft durch verdünnte Mineralsäure.
Die neue Verbindung, die nach dem Um kristallisieren aus Benzol-Petroläther den Schmelzpunkt 73-74o zeigt, bildet farblose Kristalle. Sie soll therapeutische Verwendung finden. <I>Beispiel:</I> 10 gr Natrium werden in 250 cm' abso lutem Alkohol gelöst, dann mit 20 gr Methyl- harnstoff und 44 gr des Äthyl-(methyl-d-1.2- cyclopentenyl)-cyanessigsäureäthylesters,
wie er erhältlich ist durch Kondensation von 3- Methyl-cyclopentanon mit Cyanessigsäure- äthylester und Äthylierung des dabei ent standenen (11Zethyl-d-1.2-cyclopentenyl)-cyan- essigsäureesters, 10 Stunden unter Rückfluss zum Sieden erhitzt. Dann wird der Alkohol abdestilliert und der Rückstand mit 200 eins 25 /oiger Schwefelsäure 7 Stunden verkocht.
Man saugt ab, wäscht mit Wasser und kri stallisiert aus Benzol unter Zusatz von Petrol-" äther um. Man erhält farblose Kristalle vom Schmelzpunkt<B>73-740.</B> PATENTANSPRUCH: Verfahren zur Darstellung einer C-Äthyl- C - (methyl-d-1. 2 - cyclopentenyl)-N- methyl- barbitursäure, dadurch gekennzeichnet, dass man Monomethylharnstoff und einen Äthyl- (methyl-d-1. 2-cyclopentenyl)-cyanessigsäure- ester,
wie er erhältlich ist durch Konden sation von 3-Methylcyclopentanon mit Cyan- essigsäureester und Äthylierung des dabei entstandenen (Methyl-d-1.2-cyclopentenyl)- eyanessigsäureesters, in Gegenwart eines Kon densationsmittels kondensiert- und das .ent standene Zwischenprodukt verseift.
Die neue Verbindung, die bei<B>73-740</B> schmilzt, bildet farblose Kristalle und soll therapeutische Verwendung finden.
Process for the preparation of an N-alkylated derivative of barbituric acid. The main patent relates to a process for the preparation of an N-alkylated C-disubstituted barbituric acid.
The subject of the present patent is a process for the preparation of a C-ethyl-C - (methyl-d-1.2 - cyclopentenyl) - N-methyl barbituric acid. The process is characterized in that an ethyl (methyl-d-1.2-cyclopentenyl) -cyanoacetic acid ester,
as obtainable by condensation of 3-methyl-cyclopentanone with cyanoacetic acid ester and ethylation of the resulting (methyl-d-1,2-cyclopentenyl) -cyanoacetic acid ester with monomethylurea in the presence of a condensing agent condensed and the resulting intermediate product to the C-Me- ethyl -C- (methyl-d-1. 2 - cyclopentenyl)
-N-methylbarbituric acid saponified.
Metal alcoholates, in particular those of the alkali metals, are expediently used as condensation agents. It is advantageous as a diluent an alcohol such. B. ethyl alcohol to add. The saponification is advantageously carried out using dilute mineral acid.
The new compound, which after crystallizing from benzene petroleum ether shows the melting point 73-740, forms colorless crystals. It should find therapeutic use. <I> Example: </I> 10 grams of sodium are dissolved in 250 cm of absolute alcohol, then with 20 grams of methyl urea and 44 grams of ethyl (methyl-d-1.2-cyclopentenyl) -cyanoacetate,
as obtainable by condensation of 3-methyl-cyclopentanone with ethyl cyanoacetate and ethylation of the resulting (11Zethyl-d-1,2-cyclopentenyl) -cyanoacetic acid ester, heated to boiling under reflux for 10 hours. The alcohol is then distilled off and the residue is boiled for 7 hours with 200 liters of 25% sulfuric acid.
It is filtered off with suction, washed with water and crystallized from benzene with the addition of petroleum ether. Colorless crystals with a melting point of <B> 73-740 are obtained. </B> PATENT CLAIM: Process for the preparation of a C-ethyl C - (methyl-d-1. 2 - cyclopentenyl) -N-methyl barbituric acid, characterized in that monomethyl urea and an ethyl (methyl-d-1. 2-cyclopentenyl) -cyanoacetic acid ester,
as it is obtainable by condensation of 3-methylcyclopentanone with cyanoacetic acid ester and ethylation of the resulting (methyl-d-1,2-cyclopentenyl) - eyanessigsäureester, condensed in the presence of a condensing agent and the .ent stood saponified intermediate.
The new compound, which melts at <B> 73-740 </B>, forms colorless crystals and is said to find therapeutic use.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE168366X | 1931-05-16 | ||
| CH163696T | 1932-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH168366A true CH168366A (en) | 1934-03-31 |
Family
ID=25717852
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH168366D CH168366A (en) | 1931-05-16 | 1932-05-14 | Process for the preparation of an N-alkylated derivative of barbituric acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH168366A (en) |
-
1932
- 1932-05-14 CH CH168366D patent/CH168366A/en unknown
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