CH311614A

CH311614A - Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

Info

Publication number: CH311614A
Authority: CH
Inventors: Aktiengesellschaft Cilag
Original assignee: Cilag Ag
Priority date: 1952-02-25
Filing date: 1952-02-25
Publication date: 1955-11-30

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), welehes dadurch gekennzeich-    net ist, dass man eine Verbindung der Formel
EMI1.1     
 in weleher X einen reaktionsfähigen, während der Reaktion sieh abspaltenden Rest, bedeutet, mit Benzylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austausch gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsul  fonyloxy-oder Arylsulfonyloxygruppe,    bestehen. Der Austausch der Gruppe X gegen den Benzylaminrest erfolgt z. B. durch einfaches Erwärmen mit Benzylamin gegebenenfalls in Gegenwart eines basisch reagierenden   Konden-    sationsmittels oder von Benzylamin im Überschuss. Das   Benzylaminoacet- (2-ehlor-6-methyl-    anilid) ist ein farbloses   61.    Das   Hydroehlorid    der Base sehmilzt bei 237-238  unter Zersetzung.



   Das neue   Anilid    soll als   Lokalanästhetikmn    und als Zwischenprodukt zur Herstellung weiterer Derivate Verwendung finden.



   Beispiel:
36 Gewichtsteile   Chloracet- (2-chlor-6-me-    thyl-anilid) (gewonnen durch Umsetzen von 2   Chlor-6-methyl-anilin mit Chloracetylehlorid    in Gegenwart von   Natriumacetat, Schmp. 140    bis   141 )    werden in 80 Gewichtsteilen Äthanol suspendiert und mit 54 Gewichtsteilen Benzylamin versetzt. Die Temperatur steigt dabei leicht an und ein grosser Teil des   Reaktions-    gemisches geht in   Losung.    Nun wird während 4 Stunden bei Zimmertemperatur gerührt und dann einige Stunden bei Siedetemperatur. Mit Wasserdampf wird hiera. uf der Alkohol und das überschüssige Benzylamin abgeblasen und nach dem Erkalten   das zurückbleibende 0l in    Äther aufgenommen.

   Nach dem Trocknen der ätherischen Losung und Verjagen des Lo  sungsmittels    verbleibt ein   öl,    das   durch Uber-    führung in das Hydrochlorid gereinigt wird.



  Man erhält 40   Gewiehtsteile    reines Benzylamino-acet- (2-chlor-6-methyl-anilid). Die Umsetzung mit Benzylamin kann auch in Benzol stattfinden.  



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten   Fettsäure- (2-halogen-6-       methyl-anilids), 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 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 is a reactive radical which is split off during the reaction and is reacted with benzylamine.



   The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as. B. an alkyl sulfonyloxy or aryl sulfonyloxy group exist. The exchange of group X against the benzylamine radical takes place z. B. by simply heating with benzylamine, possibly in the presence of a basic condensing agent or benzylamine in excess. Benzylaminoacet- (2-chloro-6-methyl anilide) is a colorless 61. The hydrochloride of the base melts at 237-238 with decomposition.



   The new anilide is said to be used as a local anesthetic and as an intermediate for the production of other derivatives.



   Example:
36 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are suspended in 80 parts by weight of ethanol and mixed with 54 parts by weight of benzylamine. 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 boiling temperature. With steam here a. The alcohol and the excess benzylamine are blown off and after cooling the remaining oil is taken up in ether.

   After the ethereal solution has dried and the solvent has been driven off, an oil remains, which is purified by being converted into the hydrochloride.



  40 parts by weight of pure benzylamino-acet- (2-chloro-6-methyl-anilide) are obtained. The reaction with benzylamine can also take place in benzene.



   PATENT CLAIM:
Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that a compound of the formula
EMI1.2
 

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims

** WARNING ** Beginning of CLMS field could overlap end of DESC **.

Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide).

The subject 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 is a reactive radical which is split off during the reaction and is reacted with benzylamine.

The radical X can be in a halogen atom or any other reactive substituent suitable for replacement with the basic radical, such as. B. an alkyl sulfonyloxy or aryl sulfonyloxy group exist. The exchange of group X against the benzylamine radical takes place z. B. by simply heating with benzylamine, possibly in the presence of a basic condensing agent or benzylamine in excess. Benzylaminoacet- (2-chloro-6-methyl anilide) is a colorless 61. The hydrochloride of the base melts at 237-238 with decomposition.

The new anilide is to be used as a local anesthetic and as an intermediate for the production of other derivatives.

Example: 36 parts by weight of chloroacet- (2-chloro-6-methyl-anilide) (obtained by reacting 2-chloro-6-methyl-aniline with chloroacetyl chloride in the presence of sodium acetate, melting point 140 to 141) are suspended in 80 parts by weight of ethanol and mixed with 54 parts by weight of benzylamine. 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 boiling temperature. With steam here a. The alcohol and the excess benzylamine are blown off 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 being converted into the hydrochloride.

40 parts by weight of pure benzylamino-acet- (2-chloro-6-methyl-anilide) are obtained. The reaction with benzylamine can also take place in benzene.

PATENT CLAIM: Process for the preparation of a new basic substituted fatty acid (2-halogen-6-methyl-anilide), characterized in that a compound of the formula EMI1.2 in which X is a reactive radical which is split off during the reaction and is reacted with benzylamine. The benzylaminoacet- (2-chloro-6-methylanilide) obtained in this way forms a colorless 61. The hydrochloride of the base melts below 237-238 Decomposition.

The new anilide will be used as a local anesthetic and as an intermediate product.

SUBSTANTIAL CLAIM: Process based on patent claim, characterized in that a halogenate (9-chloro-methyl-anilide) is allowed to react with benzylamine.