CH311633A - 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
CH311633A
CH311633A CH311633DA CH311633A CH 311633 A CH311633 A CH 311633A CH 311633D A CH311633D A CH 311633DA CH 311633 A CH311633 A CH 311633A
Authority
CH
Switzerland
Prior art keywords
anilide
methyl
isobutylamine
halogen
fatty acid
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cilag Ag filed Critical Cilag Ag
Publication of CH311633A publication Critical patent/CH311633A/en

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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

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  • 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 gekennzeichnet ist, dass man eine Verbindmg der Formel
EMI1.1     
   in welcher X einen reaktionsfÏhigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Isobutylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austauseh gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfonyloxy-oder Arylsulfonyloxygruppe, bestehen. Der Austausch der Gruppe X gegen den Isobutylaminrest erfolgt z. B. durch einfaches Erwärmen mit Isobutylamin gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels oder von Isobutylamin im Überschuss. Das N-Isobutyl-aminoessigsäure- (2-chlor-6-methyl-anilid) ist ein Öl, das naeh einiger Zeit zu farblosen Kristallen erstarrt.



  Das Hydroehlorid der Base schmilzt bei 207 bis 209 .



   Mit Wasserdampf wird hierauf der Alkohol und das überschüssige Isobutylamin abge blasen und nach dem Erkalten das zurück bleibende 01 in Xther aufgenommen. Nach dem
Troeknen der ätherischen Losung und Ver jagen des Lösungsmittels verbleibt ein 61, das ¯tha- Vakuumdestillation gereinigt wird.



   Man erhält 42 Gewichtsteile reines N-Isobutyl aminoessigsäure-(2-ehlor-6-methyl-anilid). Die
Umsetzung mit Isobutylamin kann auch in
Benzol stattfinden.  



   PATENTANSPRUCH :
Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure- (2-halogen-6- methyl-anilids), dadurch gekennzeiehnet, 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 production 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, reacts with isobutylamine.



   The radical X can be in a halogen atom or any other suitable reactive substituent for exchange with the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the isobutylamine residue takes place, for. B. by simply heating with isobutylamine, optionally in the presence of a basic condensing agent or of isobutylamine in excess. N-Isobutyl-aminoacetic acid (2-chloro-6-methyl-anilide) is an oil that solidifies to colorless crystals after a while.



  The hydrochloride of the base melts at 207 to 209.



   The alcohol and the excess isobutylamine are then blown off with steam and, after cooling, the remaining oil is taken up in Xther. After this
Drying the ethereal solution and expelling the solvent leaves a 61 that is cleaned ¯tha vacuum distillation.



   42 parts by weight of pure N-isobutylaminoacetic acid (2-chloro-6-methyl-anilide) are obtained. The
Implementation with isobutylamine can also be used in
Benzene take place.



   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 (1)

**WARNUNG** Anfang CLMS Feld konnte Ende DESC uberlappen **. ** WARNING ** Beginning of CLMS field could overlap end of DESC **. Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure (2-halogen-6-methyl-anilids). Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). Gegenstand des vorliegenden Patentes bildet ein Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure-(2-halogen-6 methyl-anilids), welches dadurch gekennzeichnet ist, dass man eine Verbindmg der Formel EMI1.1 in welcher X einen reaktionsfÏhigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Isobutylamin umsetzt. The subject of the present patent is a process for the production 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, reacts with isobutylamine. Der Rest X kann in einem Halogenatom oder einem sonstigen für den Austauseh gegen den basischen Rest geeigneten reaktionsfähigen Substituenten, wie z. B. einer Alkylsulfonyloxy-oder Arylsulfonyloxygruppe, bestehen. Der Austausch der Gruppe X gegen den Isobutylaminrest erfolgt z. B. durch einfaches Erwärmen mit Isobutylamin gegebenenfalls in Gegenwart eines basisch reagierenden Kondensationsmittels oder von Isobutylamin im Überschuss. Das N-Isobutyl-aminoessigsäure- (2-chlor-6-methyl-anilid) ist ein Öl, das naeh einiger Zeit zu farblosen Kristallen erstarrt. The radical X can be in a halogen atom or any other suitable reactive substituent for exchange with the basic radical, such as e.g. B. an alkylsulfonyloxy or arylsulfonyloxy group exist. The exchange of group X against the isobutylamine residue takes place, for. B. by simply heating with isobutylamine, optionally in the presence of a basic condensing agent or of isobutylamine in excess. N-Isobutyl-aminoacetic acid (2-chloro-6-methyl-anilide) is an oil that solidifies to colorless crystals after a while. Das Hydroehlorid der Base schmilzt bei 207 bis 209 . The hydrochloride of the base melts at 207 to 209. Mit Wasserdampf wird hierauf der Alkohol und das überschüssige Isobutylamin abge blasen und nach dem Erkalten das zurück bleibende 01 in Xther aufgenommen. Nach dem Troeknen der ätherischen Losung und Ver jagen des Lösungsmittels verbleibt ein 61, das ¯tha- Vakuumdestillation gereinigt wird. The alcohol and the excess isobutylamine are then blown off with steam and, after cooling, the remaining oil is taken up in Xther. After this Drying the ethereal solution and expelling the solvent leaves a 61 that is cleaned ¯tha vacuum distillation. Man erhält 42 Gewichtsteile reines N-Isobutyl aminoessigsäure-(2-ehlor-6-methyl-anilid). Die Umsetzung mit Isobutylamin kann auch in Benzol stattfinden. 42 parts by weight of pure N-isobutylaminoacetic acid (2-chloro-6-methyl-anilide) are obtained. The Implementation with isobutylamine can also be used in Benzene take place. PATENTANSPRUCH : Verfahren zur Herstellung eines neuen basisch substituierten Fettsäure- (2-halogen-6- methyl-anilids), dadurch gekennzeiehnet, dass man eine Verbindung der Formel EMI1.2 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Isobut-ylamin umsetzt. Das aui' diese'eise erhaltene N-Isobutyl-amino-essig- durch ein Öl, das nach einiger Zeit zu farblosen Kristallen erstarrt. Das Hydroehlorid der Base sehmilzt bei sÏure-(2-chlor-6-methyl-anilid) bildet Das 207-209¯. Anilid soll als Lokalanästhetikum und als Zwisehenprodukt Verwendung finden. 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, is reacted with isobutylamine. The N-isobutyl-amino-vinegar obtained in this way is produced by an oil that solidifies to colorless crystals after a while. The hydrochloride of the base melts with acid (2-chloro-6-methyl-anilide) The 207-209¯. Anilide is said to be used as a local anesthetic and as an intermediate product. UNTERAN : Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man ein Halogenacet- (2 chlor-6-methyl-anilid) mit Isobutvlamin rea gieren neue BELOW: Process according to patent claim, characterized in that a halogenacet- (2 chloro-6-methyl-anilide) react with isobutylamine new
CH311633D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311633A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311633T 1952-02-25
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311633A true CH311633A (en) 1955-11-30

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ID=25735366

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311633D CH311633A (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) CH311633A (en)

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