CH264828A - Process for the preparation of 3,5-dimethyl-oxazolidine-2,4-dione. - Google Patents
Process for the preparation of 3,5-dimethyl-oxazolidine-2,4-dione.Info
- Publication number
- CH264828A CH264828A CH264828DA CH264828A CH 264828 A CH264828 A CH 264828A CH 264828D A CH264828D A CH 264828DA CH 264828 A CH264828 A CH 264828A
- Authority
- CH
- Switzerland
- Prior art keywords
- dione
- oxazolidine
- dimethyl
- sep
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- PBZJGICLVHLSSJ-UHFFFAOYSA-N 3,5-dimethyl-1,3-oxazolidine-2,4-dione Chemical compound CC1OC(=O)N(C)C1=O PBZJGICLVHLSSJ-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 3
- -1 methyl halide Chemical class 0.000 claims description 6
- ZBBUWSWHUXAKGA-UHFFFAOYSA-N 5-methyl-1,3-oxazolidine-2,4-dione Chemical compound CC1OC(=O)NC1=O ZBBUWSWHUXAKGA-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung von 3,5-Dimethyl-oxazolidin-2,4-dion. Das Hauptpatent betrifft ein Verfahren zur Herstellung von 3,5,5-Trimethyl-oxazoli- din-2,4-dion, einer Substanz mit zuckungs- und krampfhindernder Wirkung. Es wurde gefun den, dass durch Einführung einer Methyl- gruppe in der 3-Stellung von 5-Methyl-oxazoli- din-2,4-dion ebenfalls eine Substanz mit dieser Wirkung erhalten wird.
Gegenstand des vorliegenden Patentes ist somit ein Verfahren zur Herstellung von 3,5- Dimethyl-oxazolidin-2,4-dion, welches dadurch gekennzeichnet ist, dass man eine Substanz der Formel
EMI0001.0012
worin X einen bei der Reaktion sich abspal tenden Rest bedeutet, mit einem Methylie- rungsmittel behandelt.
<I>Beispiel:</I> 22 g 5-Methyl-oxazolidin-2,4-dion werden mit ungefähr 26,5 g Dimethylsulfat in einer wässerigen Reaktionsmischung, enthaltend un gefähr 9,2 g Natriumhydroxyd, behandelt. Durch Abkühlung des Reaktionsgefässes und tropfenweise Zugabe des Dimethylsulfats wird dafür gesorgt, dass die Temperatur des Reak tionsgutes nicht über 500 C ansteigt. Es wird mit Äther extrahiert, der Äther in üblicher Weise entfernt und der gewonnene Extrakt destilliert.
Das Endprodukt, 3,5-Dimethyl-oxa- zolidin-2,4-dion, wird in Form eines farblosen Üls mit einem Siedepunkt zwischen 75 und 830 C bei 4 mm Druck und 1380 C bei 50 mm Druck erhalten.
Das 3,5-Dimethyl-oxazolidin-2,4-dion kann auch durch Umsetzung eines Alkalimetallsal- zes des 5-lvlethyl-oxazolidin-2,4-dions mit Di- methyIsulfat oder einem Methylhalogenid oder durch Umsetzung des Silbersalzes des 5- Methyl-oxazolidin-2,4-dions mit einem Methyl- halogenid erhalten werden.
Als Alkalimetall- salz wird vorzugsweise das Natriumsalz und als Methylhalogenid das Methyljodid ver wendet.
Process for the preparation of 3,5-dimethyl-oxazolidine-2,4-dione. The main patent relates to a process for the production of 3,5,5-trimethyl-oxazolidine-2,4-dione, a substance with anti-twitch and cramp-preventing effects. It was found that the introduction of a methyl group in the 3-position of 5-methyl-oxazolin-2,4-dione also gives a substance with this effect.
The present patent thus relates to a process for the preparation of 3,5-dimethyl-oxazolidine-2,4-dione, which is characterized in that a substance of the formula
EMI0001.0012
where X is a radical which splits off during the reaction, treated with a methylation agent.
<I> Example: </I> 22 g of 5-methyl-oxazolidine-2,4-dione are treated with approximately 26.5 g of dimethyl sulfate in an aqueous reaction mixture containing approximately 9.2 g of sodium hydroxide. By cooling the reaction vessel and adding the dimethyl sulfate drop by drop, it is ensured that the temperature of the reac tion material does not rise above 500 C. It is extracted with ether, the ether is removed in the usual way and the extract obtained is distilled.
The end product, 3,5-dimethyl-oxazolidine-2,4-dione, is obtained in the form of a colorless oil with a boiling point between 75 and 830 ° C. at 4 mm pressure and 1380 ° C. at 50 mm pressure.
The 3,5-dimethyl-oxazolidine-2,4-dione can also be obtained by reacting an alkali metal salt of 5-methyl-oxazolidine-2,4-dione with dimethyl sulfate or a methyl halide or by reacting the silver salt of 5-methyl -oxazolidine-2,4-dione can be obtained with a methyl halide.
The sodium salt is preferably used as the alkali metal salt and the methyl iodide is used as the methyl halide.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US264828XA | 1941-07-18 | 1941-07-18 | |
| CH258454T | 1946-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH264828A true CH264828A (en) | 1949-10-31 |
Family
ID=25730175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264828D CH264828A (en) | 1941-07-18 | 1946-03-11 | Process for the preparation of 3,5-dimethyl-oxazolidine-2,4-dione. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH264828A (en) |
-
1946
- 1946-03-11 CH CH264828D patent/CH264828A/en unknown
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