CH311620A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). - Google Patents
Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).Info
- Publication number
- CH311620A CH311620A CH311620DA CH311620A CH 311620 A CH311620 A CH 311620A CH 311620D A CH311620D A CH 311620DA CH 311620 A CH311620 A CH 311620A
- Authority
- CH
- Switzerland
- Prior art keywords
- anilide
- methyl
- halogen
- fatty acid
- production
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 4
- 239000000194 fatty acid Substances 0.000 title claims description 4
- 229930195729 fatty acid Natural products 0.000 title claims description 4
- 150000004665 fatty acids Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000003931 anilides Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000012230 colorless oil Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- WFNLHDJJZSJARK-UHFFFAOYSA-N 2-chloro-6-methylaniline Chemical compound CC1=CC=CC(Cl)=C1N WFNLHDJJZSJARK-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005292 vacuum distillation 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 Herstellung eines neuen basisch substituierten Fettsäure (2-halogen-6-methyl-anilids). Gegenstand des, vorliegenden Patentes bil det ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen 6- methZ-l-a.nilids), welches dadurch gekennzeich net ist, dass man eine Verbindung der Formel
EMI0001.0008
in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Allylamin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basisehen Rest geeigneten reaktionsfähi gen Substituenten, wie z. B. einer Alkylsul- fonyloxy- oder Arylsulfonyloxygruppe, beste hen. Der Austausch der Gruppe X gegen den Allylaminrest erfolgt z.
B. durch einfaches Erwärmen mit Allylamin gegebenenfalls in Gegenwart eines basisch reagierenden Kon densationsmittels oder von Allvlamin im L\ber- scbuss. Das Allylaminoacet-(2-chlor-6-methyl- anilid) ist ein farbloses Öl. Das Hydrochlorid der Base schmilzt bei 260-263 unter Zer setzung.
Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung wei terer Derivate Verwendung finden. Beispiel: 36 Gewichtsteile Chloracet-(2-chlor-6-me- thylanilid) (gewonnen durch Umsetzen von 2 Chlor-6-methyl-anilin mit.
Chloracetylchlorid in Gegenwart von Natriumacetat, Schmp. 140 bis 141 ) werden in 80 Gewichtsteilen Äthanol suspendiert und mit 40 Gewichtsteilen<B>Al</B> yl- amin versetzt. Die Temperatur steigt dabei leicht an und ein grosser Teil des Reaktions gemisches geht in Lösung. Nun wird während 4 Stunden bei Zimmertemperatur gerührt und dann einige Stunden bei 65-75 .
Eine Probe mit Wasser und nachfolgend mit verdünnter Salzsäure versetzt ergibt. wieder Lösung des ausgefallenen Niederschlages. Mit Wasser dampf wird hierauf der Alkohol und das überschüssige Allylamin abgeblasen und nach dem Erkalten das zurückbleibende Öl in Äther aufgenommen. Nach dem Trocknen der ätherischen Lösung und Verjagen des Lö sungsmittels verbleibt ein Öl, das durch Vakuumdestillation gereinigt wird. Man erhält 37 Gewichtsteile reines Allylaminoacet- (2- ehlor-6-methyl-anilid). Die Umsetzung mit.
Allylamin kann auch in Benzol stattfinden.
Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). Subject of the present patent bil det a process for the preparation of a new basic substituted fatty acid (2-halogen 6-methZ-1-a.nilids), which is characterized in that a compound of the formula
EMI0001.0008
in which X is a reactive radical that is split off during the reaction, reacts with allylamine.
The radical X can be in a halogen atom or other reactive substituents suitable for replacement with the basic radical, such as. B. an alkylsulfonyloxy or arylsulfonyloxy group, best hen. The exchange of group X against the allylamine residue takes place, for.
B. by simply heating with allylamine, optionally in the presence of a basic reacting condensation agent or of allvlamin in the L \ ber- scbuss. Allylaminoacet- (2-chloro-6-methyl-anilide) is a colorless oil. The hydrochloride of the base melts at 260-263 with decomposition.
The new anilide is to be used as a local anesthetic and as an intermediate for the production of further derivatives. Example: 36 parts by weight of chloroacet- (2-chloro-6-methylanilide) (obtained by reacting 2 chloro-6-methyl-aniline with.
Chloracetyl chloride in the presence of sodium acetate, melting point 140 to 141) are suspended in 80 parts by weight of ethanol and 40 parts by weight of Al ylamine are added. The temperature rises slightly and a large part of the reaction mixture goes into solution. The mixture is then stirred for 4 hours at room temperature and then for a few hours at 65-75.
A sample with water and then mixed with dilute hydrochloric acid results. again dissolution of the precipitate. The alcohol and the excess allylamine are then blown off with steam and, after cooling, the remaining oil is absorbed in ether. After the essential solution has dried and the solvent has been driven off, an oil remains which is purified by vacuum distillation. 37 parts by weight of pure allylaminoacet- (2-chloro-6-methyl-anilide) are obtained. Implementation with.
Allylamine can also take place in benzene.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311620T | 1952-02-25 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311620A true CH311620A (en) | 1955-11-30 |
Family
ID=25735353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311620D CH311620A (en) | 1952-02-25 | 1952-02-25 | Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH311620A (en) |
-
1952
- 1952-02-25 CH CH311620D patent/CH311620A/en unknown
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