CH220960A - Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine. - Google Patents
Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine.Info
- Publication number
- CH220960A CH220960A CH220960DA CH220960A CH 220960 A CH220960 A CH 220960A CH 220960D A CH220960D A CH 220960DA CH 220960 A CH220960 A CH 220960A
- Authority
- CH
- Switzerland
- Prior art keywords
- dioxo
- preparation
- diethylpyrrolidine
- ammonia
- diethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- OVYXIRRFXWBHKF-UHFFFAOYSA-N 3,3-diethylpyrrolidine-2,4-dione Chemical compound CCC1(CC)C(=O)CNC1=O OVYXIRRFXWBHKF-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 230000000517 effect on sleep Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- ALJYEUBPKWZWMK-UHFFFAOYSA-N 3,3-dipropylpyrrolidine-2,4-dione Chemical compound O=C1NCC(C1(CCC)CCC)=O ALJYEUBPKWZWMK-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/38—2-Pyrrolones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Darstellung von 2,4-Dioxo-3,3-cliätliylpyrrolidin. Nach dem Verfahren des Hauptpatentes wird 2,4-Dioxo-3,3-di-n-propyl-pyrrolidin da durch gewonnen, dass auf a,a-Di-n-propyl-y- halogenacetessigester in Anwesenheit eines Lösungsmittels Ammoniak einwirken gelas sen wird.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung von 2,4-Dioxo- 3,3-diäthyl-pyrrolidin, welches dadurch ge kennzeichnet ist, dass auf a,a-Diäthyl-y-halo- genacetessigester in Anwesenheit eines Lö sungsmittels Ammoniak einwirken gelassen wird.
Das bisher unbekannte 2,4-Dioxo-3,3-di- äthyl-pyrrolidin bildet farblose Kristalle, die bei 88 bis 89 schmelzen. Es siedet bei 12 mm Druck zwischen 175 bis<B>1-78.'</B> und ist in Wasser, sowie in den üblichen organischen Lösungsmitteln leicht löslich. Da--es Schlaf wirkung besitzt, soll es als Arzneimittel ver wendet werden.
<I>Beispiel:</I> Man leitet unter guter Kühlung in 350 Teile Alkohol 70 Teile Ammoniakgas ein. Zu dem noch kalten, alkoholischen Ammoniak gibt man auf einmal 265 Teile a,a-Diäthyl- y-brom-acetessigester. Nach einiger Zeit er wärmt sich die Lösung ganz langsam und bald beginnt die Ausscheidung von Ammo- niumbromid. Nach 24 Stunden werden das überschüssige Ammoniakgäs und der Alkohol im Vakuum abdestilliert. - Der Rückstand wird zweimal mit 200 Teilen Benzol-Alkohol- Gemisch (1 :
1) ausgekocht und das ungelöste Ammoniumbromid abgetrennt. Der nach dem Vertreiben des Lösungsmittels verblei bende ölige Rückstand.wird im Vakuum de stilliert. Das sofort fest werdende Destillat wird in der doppelten Menge Benzol warm gelöst und die Lösung bis zur Trübung mit Petroläther versetzt, worauf sich Kristalle ausscheiden.
Process for the preparation of 2,4-dioxo-3,3-cliätliylpyrrolidin. According to the process of the main patent, 2,4-dioxo-3,3-di-n-propyl-pyrrolidine is obtained by the fact that a, a-di-n-propyl-y-haloacetoacetic ester in the presence of a solvent ammonia act sen becomes.
The subject of the present patent is a process for the preparation of 2,4-dioxo-3,3-diethyl-pyrrolidine, which is characterized in that a, a-diethyl-y-haloacetoacetic ester acts in the presence of a solvent, ammonia is left.
The previously unknown 2,4-dioxo-3,3-diethylpyrrolidine forms colorless crystals that melt at 88 to 89. At 12 mm pressure it boils between 175 to <B> 1-78. '</B> and is easily soluble in water as well as in common organic solvents. Since it has a sleep effect, it should be used as a medicine.
<I> Example: </I> 70 parts of ammonia gas are introduced into 350 parts of alcohol with good cooling. 265 parts of α, α-diethyl-γ-bromo-acetoacetic ester are added all at once to the still cold, alcoholic ammonia. After a while the solution warms up very slowly and soon the ammonium bromide begins to excrete. After 24 hours, the excess ammonia and the alcohol are distilled off in vacuo. - The residue is washed twice with 200 parts of a benzene-alcohol mixture (1:
1) boiled and the undissolved ammonium bromide separated. The oily residue remaining after the solvent has been driven off is distilled in vacuo. The distillate, which solidifies immediately, is dissolved in double the amount of warm benzene and petroleum ether is added to the solution until it becomes cloudy, whereupon crystals separate out.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE220960X | 1938-11-30 | ||
| CH213347T | 1939-10-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH220960A true CH220960A (en) | 1942-04-30 |
Family
ID=25725409
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH220960D CH220960A (en) | 1938-11-30 | 1939-10-13 | Process for the preparation of 2,4-dioxo-3,3-diethylpyrrolidine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH220960A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727897A (en) * | 1952-02-08 | 1955-12-20 | Ciba Pharm Prod Inc | Dioxo-pyrrolidines |
-
1939
- 1939-10-13 CH CH220960D patent/CH220960A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2727897A (en) * | 1952-02-08 | 1955-12-20 | Ciba Pharm Prod Inc | Dioxo-pyrrolidines |
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