CH311631A - 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
- CH311631A CH311631A CH311631DA CH311631A CH 311631 A CH311631 A CH 311631A CH 311631D A CH311631D A CH 311631DA CH 311631 A CH311631 A CH 311631A
- Authority
- CH
- Switzerland
- Prior art keywords
- anilide
- methyl
- methylamine
- halogen
- chloro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 7
- 229930195729 fatty acid Natural products 0.000 title claims description 7
- 239000000194 fatty acid Substances 0.000 title claims description 7
- 150000004665 fatty acids Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003931 anilides Chemical class 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 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
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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 bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6 methyl-anilids), welches dadurch gekennzeich- net ist, dass man eine Verbindung der Formel
EMI1.1
in welcher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest bedeutet, mit Methylamin umsetzt.
Der Rest X kann in einem Halogenatom oder einem sonstigen f r den Austausch gegen den basisehen Rest geeigneten reaktionsfähi- gen Substituenten, wie z. B. einer Alkylsulfo nvloxy-oder Arylsulfonyloxygruppe bestehen.
Der Austausch der Gruppe X gegen den Me thylaminrest erfolgt z. B. durch einfaches Er värmen mit hIethylamin gegebenenfalls in Gegenwart eines basisch reagierenden Konden sationsmittels oder von Methylamin im ¯ber schuss. Das ¯-Methylamino-propionsÏure-(2 ehlor-6-methyl-anilid) ist ein öl, das nach einiger Zeit zu farblosen Kristallen erstarrt. Das Hydrochlorid der Base schmilzt bei 173, 5 bis 174 .
Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendmg finden.
Beispiel :
40 Gewichtsteile ¯-Chlor-propionsÏure-(2 ehlor-6-methyl-anilid) werden in 100 Gewichts- teilen Methanol suspendiert und mit 140 Ge wichtsteilen Methylaminlösung versetzt. Die Temperatur steigt dabei leicht an, und ein grosser Teil des Reaktionsgemisehes geht in Lösung. Nun wird während 4 Stunden bei Zimmertemperatur gerührt und dann einige Stunden unter Druck bei 100-110¯. Mit Wasserdampf wird hierauf der Alkohol und das übersehüssige Methylamin abgeblasen und nach dem Erkalten das zurüekbleibende öl in Äther aufgenommen. Nach dem Trocknen der ätherischen Losung und Verjagen des Lösungsmittels verbleibt ein öl, das durch Uberführen in das Hydrochlorid gereinigt wird.
Man erhält 30 Gewichtsteile reines B-Methyl- amino-propionsäure- (2-chlor-6-methyl-anilid).
Die Umsetzung mit Methylamin kann auch in Benzol stattfinden.
PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure- (2-halogen-6- methylanilids), dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.2
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).
The subject matter of the present patent is a process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), which is characterized in that a compound of the formula
EMI1.1
in which X denotes a reactive radical which is split off during the reaction, with methylamine.
The radical X can be in a halogen atom or another reactive substituent suitable for replacement with the basic radical, such as B. an Alkylsulfo nvloxy or Arylsulfonyloxygruppe exist.
The exchange of group X against the Me thylaminrest takes place z. B. by simply heating it with methylamine, possibly in the presence of a basic condensation agent or of methylamine in excess. The ¯-methylamino-propionic acid (2 chloro-6-methyl-anilide) is an oil that solidifies to colorless crystals after a while. The hydrochloride of the base melts at 173.5-174.
The new anilide is said to be used as a local anesthetic and as an intermediate for the production of other derivatives.
Example:
40 parts by weight of ¯-chloropropionic acid (2 chloro-6-methyl-anilide) are suspended in 100 parts by weight of methanol and 140 parts by weight of methylamine solution 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 under pressure at 100-110¯. The alcohol and excess methylamine are then blown off with steam and, after cooling, the remaining oil is absorbed in ether. After the ethereal solution has dried and the solvent has been driven off, an oil remains which is purified by converting it into the hydrochloride.
30 parts by weight of pure B-methylamino-propionic acid (2-chloro-6-methyl-anilide) are obtained.
The reaction with methylamine can also take place in benzene.
PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid (2-halo-6-methylanilide), characterized in that a compound of the formula
EMI1.2
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH311631T | 1952-02-25 | ||
| CH307799T | 1952-11-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH311631A true CH311631A (en) | 1955-11-30 |
Family
ID=25735364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH311631D CH311631A (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) | CH311631A (en) |
-
1952
- 1952-02-25 CH CH311631D patent/CH311631A/en unknown
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