CH190643A - Process for the preparation of the di-n-propylamide of 3,5-dimethyl-isoxazole-4-carboxylic acid. - Google Patents
Process for the preparation of the di-n-propylamide of 3,5-dimethyl-isoxazole-4-carboxylic acid.Info
- Publication number
- CH190643A CH190643A CH190643DA CH190643A CH 190643 A CH190643 A CH 190643A CH 190643D A CH190643D A CH 190643DA CH 190643 A CH190643 A CH 190643A
- Authority
- CH
- Switzerland
- Prior art keywords
- isoxazole
- carboxylic acid
- dimethyl
- propylamide
- preparation
- Prior art date
Links
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 title claims description 8
- IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AJJHTGVYWRKVIJ-UHFFFAOYSA-N CC1=NOC(C)=C1C(Br)=O Chemical compound CC1=NOC(C)=C1C(Br)=O AJJHTGVYWRKVIJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- UXYRXGFUANQKTA-UHFFFAOYSA-N 1,2-oxazole-3-carboxylic acid Chemical class OC(=O)C=1C=CON=1 UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 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 Darstellung des Di-n-propylamids der 3,6-Dimethyl-isoxazol-4-earbonsäure. Praktisch verwertbare Vertreter der Iso- xazolreihe sind bisher noch nicht bekannt geworden (vergleiche z. B. Meyer-Jacobson, Lehrbuch der organischen Chemie, Bd. II, dritter Teil, S. 507, letzter Abschnitt).
Es wurde nun gefunden, daZ dialkylsubstituierte Amide von Isoxazolcarbonsäuren wertvolle therapeutische Eigenschaften aufweisen. Zur Herstellung dieser Amide werden Verbin dungen der allgemeinen. Formel
EMI0001.0016
in welcher einer der Reste R1, R2, R3 eine Carboxylgruppe, die übrigen Alkylreste oder Wasserstoff bedeuten, in umsetzungsfähige Säureabkömmlinge, z. B. in :die bisher noch unbekannten Säurechloride übergeführt und diese mit sekundären Aminen umgesetzt.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Darstellung des Di-n-pro- pylamids der 3,5-Dimethyl-isoxazol-4-carbon- säure, welches dadurch gekennzeichnet ist, dass man 3;5-Dimethyl-isoxazol-4-carbonsäure, ein Kondensationsmittel und Di-n-propylamin aufeinander einwirken lässt.
Das neue Di-n-propylamid der 3,5-Dime- thyl-isoxazol-4-carbonsäure ist ein hellgelbes 01, welches bei 168 unter 13, nim Druck siedet. Es löst sich leicht in Alkohol, Äther, Benzol, Chloroform; in Wasser löst es sich nur wenig.
Es soll als Arzneimittel verwendet wer den.
<I>Beispiel:</I> 43-0 Teile Phosphorpentabromid werden mit 147 Teilen '3,5-Dimethyl-isoxazol-4-car- bonsäure gemischt und unter Ausschlu3 der Luftfeuchtigkeit allmählich auf<B>701</B> er wärmt. Nach Beendigung der Bromwasser- stoffentwicklung wird das flüssige Reak- tionsgemisch im Vakuum fraktioniert.
Unter einem Druck von 11 mm geht bei 86 bis 93 Phosphoroxybromid, bei 100 bis 11(i das 3,5 - Dimethyl-isoxazol- 4 -carbonsäurebromid über. Durch nochmalige Destillation erhält man es rein als ein schweres farbloses 01 vom Siedepunkt 10.1 bis 106 unter einem Druck von 11 mm. Die Ausbeute ist nahezu quan titativ.
205 Teile 3,5-Dimethyl-isoxazol-4-carbon- säurebromid werden unter Kühlung mit Eis und unter gutem Rühren zu einer Mischung von 101 Teilen Di-n-propylamin, 120 Teilen 20@ iger Natronlauge und 200 Teilen Äther zutropfen gelassen. Nach Beendigung der Reaktion wird die ätherische Schicht abge hoben, über wasserfreier Pottasche getrocknet und der Äther abdestilliert. Der Rückstand wird durch Destillation im Vakuum gerei nigt.
Process for the preparation of the di-n-propylamide of 3,6-dimethyl-isoxazole-4-carboxylic acid. Practically usable representatives of the isoxazole series have not yet become known (see, for example, Meyer-Jacobson, Textbook of Organic Chemistry, Vol. II, third part, p. 507, last section).
It has now been found that dialkyl-substituted amides of isoxazole carboxylic acids have valuable therapeutic properties. For the preparation of these amides, compounds of the general. formula
EMI0001.0016
in which one of the radicals R1, R2, R3 is a carboxyl group, the remaining alkyl radicals or hydrogen are converted into reactive acid derivatives, e.g. B. in: the hitherto unknown acid chlorides converted and these reacted with secondary amines.
The subject matter of the present patent is a process for the preparation of the di-n-propylamide of 3,5-dimethyl-isoxazole-4-carboxylic acid, which is characterized in that 3; 5-dimethyl-isoxazole-4-carboxylic acid is used , a condensing agent and di-n-propylamine interact.
The new di-n-propylamide of 3,5-dimethyl-isoxazole-4-carboxylic acid is a light yellow oil, which at 168 boils below 13 minutes under pressure. It easily dissolves in alcohol, ether, benzene, chloroform; it dissolves only a little in water.
It is intended to be used as a medicinal product.
<I> Example: </I> 43-0 parts of phosphorus pentabromide are mixed with 147 parts of 3,5-dimethyl-isoxazole-4-carboxylic acid and gradually heated to <B> 701 </B> with exclusion of atmospheric moisture . After the evolution of hydrogen bromide has ended, the liquid reaction mixture is fractionated in vacuo.
Under a pressure of 11 mm, phosphorus oxybromide passes over at 86 to 93, and the 3,5-dimethyl-isoxazole-4-carboxylic acid bromide at 100 to 11 (i. Another distillation gives it pure form as a heavy colorless oil with a boiling point of 10.1 to 106 under a pressure of 11 mm. The yield is almost quantitative.
205 parts of 3,5-dimethyl-isoxazole-4-carboxylic acid bromide are added dropwise while cooling with ice and with thorough stirring to a mixture of 101 parts of di-n-propylamine, 120 parts of 20% sodium hydroxide solution and 200 parts of ether. After the reaction has ended, the ethereal layer is lifted off, dried over anhydrous potash and the ether is distilled off. The residue is purified by distillation in vacuo.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE190643X | 1935-02-22 | ||
| CH185280T | 1936-01-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH190643A true CH190643A (en) | 1937-04-30 |
Family
ID=25721191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH190643D CH190643A (en) | 1935-02-22 | 1936-01-24 | Process for the preparation of the di-n-propylamide of 3,5-dimethyl-isoxazole-4-carboxylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH190643A (en) |
-
1936
- 1936-01-24 CH CH190643D patent/CH190643A/en unknown
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