CH377799A - Process for the preparation of new aryloxyacetic acid amides - Google Patents
Process for the preparation of new aryloxyacetic acid amidesInfo
- Publication number
- CH377799A CH377799A CH287464A CH287464A CH377799A CH 377799 A CH377799 A CH 377799A CH 287464 A CH287464 A CH 287464A CH 287464 A CH287464 A CH 287464A CH 377799 A CH377799 A CH 377799A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- chloride
- radical
- alkyl
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 150000001408 amides Chemical class 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 cycloalkyl radical Chemical class 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UUZNZXBSSVTRMY-UHFFFAOYSA-N 2-(4-prop-1-enyl-2-propoxyphenoxy)acetic acid Chemical compound C(CC)OC1=C(OCC(=O)O)C=CC(=C1)C=CC UUZNZXBSSVTRMY-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001514 alkali metal chloride Inorganic materials 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von neuen Aryloxyessigsäureamiden
Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung neuer Derivate von Aryloxyessigsäuren mit wertvollen pharmakologischen Eigenschaften.
Substituierte Aryloxyessigsäureamide entsprechend der Formel I
EMI1.1
worin R1 einen Alkyl-, Alkenyl- oder Cycloalkylrest oder einen gegebenenfalls durch Halogen oder niedermolekulare Alkyl- oder Alkoxygruppen substituierten Phenyl- oder Benzylrest, R2 Wasserstoff oder einen niedermolekularen Alkyl oder Alkenylrest, den Allyl- oder Propen-(l)-yl-rest und R4 einen Alkylrest mit 2-6 Kohlenstoffatomen bedeuten, wobei Alkylreste Rt und R2 auch unter sich direkt oder über ein Sauerstoffatom verbunden sein können, sind bisher nicht bekanntgeworden. Überraschenderweise wurde nun gefunden, dass diese Verbindungen pharmakologisch wertvolle Eigenschaften, insbesondere anästhetische, hypnotische, sedative und antikonvulsive Wirksamkeit besitzen.
Erfindungsgemäss stellt man die oben definierten Verbindungen her, indem man ein Carbaminylchlorid der Formel II,
EMI1.2
in der Wärme auf ein Salz einer Aryloxyessigsäure der Formel III
EMI1.3
insbesondere ein Alkalisalz einwirken lässt. Unter Entwicklung von Kohlendioxyd und Abscheidung entsprechender Chloride, z. B. Alkalimetallchloride, bilden sich die gewünschten N,N-disubstituierten Amide. Als Ausgangsstoffe der Formel II kommen beispielsweise die von den sekundären Aminen der Formel IV
EMI1.4
sich ableitenden Carbaminylchloride in Frage.
Als Beispiele der als Ausgangsstoffe in Betracht kommenden Aryloxyessigsäure der Formel III seien die
2-Athoxy-4-allyl-phenoxyessigsäure, 2-Sithoxy-4-propenyl-phenoxyessigsäure,
2-n-Propoxy-4-allyl-phenoxyessigsäure,
2-n-Propoxy-4-propenyl-phenoxyessigsäure,
2-Isopropoxy-4-allyl-phenoxyessigsäure,
2-n-Butoxy-Pallyl-phenoxyessigsäure,
2-n-Butoxy-Spropenyl-phenoxyessigsäure,
2-Isobutoxy-Sallyl-phenoxyessigsäure,
2-n-Amyloxy-4-allyl-phenoxyessigsäure,
2-n-Amyloxy-4-propenyl-phenoxyessigsäure,
2-n-Hexyloxy-4-allyl-phenoxyessigsäure und 2-n-Hexyloxy-Ppropenyl-phenoxyessigsäure genannt.
Im nachstehenden Beispiel bedeuten Teile Ge wichtsteile; diese verhalten sich zu Volumteilen wie g zu cma. Die Temperaturen sind in Celsiusgraden angegeben.
Beispiel
25,8 Teile getrocknetes Natriumsalz der 2-Äth- oxy-4-allyl-phenoxyessigsäure werden in 200 Teilen Xylol suspendiert und von der Suspension etwa 100 Teile Xylol abdestilliert. Bei 20 versetzt man die Suspension unter Rühren mit 14 Teilen Dimethylcarbaminsäurechlorid und kocht sie darauf während 4 Stunden unter Rückfluss. Nach dem Abkühlen versetzt man das Reaktionsgemisch mit Äther, wäscht es mit Wasser und verdünnter Natronlauge, trocknet es über Natriumsulfat und destilliert die Lösungsmittel im Vakuum ab. Das zurückbleibende Ö1 liefert bei der Destillation 2-Äthoxy-4-allyl-phenoxyessig- säure-dimethylamid, ein bei 132-135 l0, 005 Torr siedendes Ö1.
Process for the preparation of new aryloxyacetic acid amides
The present invention relates to a process for the preparation of new derivatives of aryloxyacetic acids with valuable pharmacological properties.
Substituted aryloxyacetic acid amides corresponding to the formula I.
EMI1.1
wherein R1 is an alkyl, alkenyl or cycloalkyl radical or a phenyl or benzyl radical optionally substituted by halogen or low molecular weight alkyl or alkoxy groups, R2 is hydrogen or a low molecular weight alkyl or alkenyl radical, the allyl or propene (l) -yl radical and R4 denotes an alkyl radical with 2-6 carbon atoms, where alkyl radicals Rt and R2 can also be connected directly to one another or via an oxygen atom, have not yet become known. Surprisingly, it has now been found that these compounds have pharmacologically valuable properties, in particular anesthetic, hypnotic, sedative and anticonvulsant activity.
According to the invention, the compounds defined above are prepared by adding a carbaminyl chloride of the formula II,
EMI1.2
in the heat to a salt of an aryloxyacetic acid of the formula III
EMI1.3
especially an alkali salt can act. With the development of carbon dioxide and the deposition of corresponding chlorides, e.g. B. alkali metal chlorides, the desired N, N-disubstituted amides are formed. Starting materials of the formula II are, for example, those of the secondary amines of the formula IV
EMI1.4
derived carbaminyl chlorides in question.
Examples of the aryloxyacetic acid of the formula III which are suitable as starting materials are the
2-ethoxy-4-allyl-phenoxyacetic acid, 2-sithoxy-4-propenyl-phenoxyacetic acid,
2-n-propoxy-4-allyl-phenoxyacetic acid,
2-n-propoxy-4-propenyl-phenoxyacetic acid,
2-isopropoxy-4-allyl-phenoxyacetic acid,
2-n-butoxy-pallyl-phenoxyacetic acid,
2-n-butoxy-propenyl-phenoxyacetic acid,
2-isobutoxy-sallyl-phenoxyacetic acid,
2-n-amyloxy-4-allyl-phenoxyacetic acid,
2-n-amyloxy-4-propenyl-phenoxyacetic acid,
2-n-hexyloxy-4-allyl-phenoxyacetic acid and 2-n-hexyloxy-propenyl-phenoxyacetic acid.
In the example below, parts mean parts by weight; these are related to parts of volume as g to cma. The temperatures are given in degrees Celsius.
example
25.8 parts of the dried sodium salt of 2-ethoxy-4-allyl-phenoxyacetic acid are suspended in 200 parts of xylene and about 100 parts of xylene are distilled off from the suspension. At 20, 14 parts of dimethylcarbamic acid chloride are added to the suspension with stirring and then refluxed for 4 hours. After cooling, the reaction mixture is treated with ether, washed with water and dilute sodium hydroxide solution, dried over sodium sulphate and the solvent is distilled off in vacuo. The remaining oil yields 2-ethoxy-4-allyl-phenoxyacetic acid dimethylamide, an oil boiling at 132-135 l0.005 torr.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH287464A CH377799A (en) | 1960-01-27 | 1960-01-27 | Process for the preparation of new aryloxyacetic acid amides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH287464A CH377799A (en) | 1960-01-27 | 1960-01-27 | Process for the preparation of new aryloxyacetic acid amides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH377799A true CH377799A (en) | 1964-05-31 |
Family
ID=4243505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH287464A CH377799A (en) | 1960-01-27 | 1960-01-27 | Process for the preparation of new aryloxyacetic acid amides |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH377799A (en) |
-
1960
- 1960-01-27 CH CH287464A patent/CH377799A/en unknown
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