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CH311603A - 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
CH311603A
CH311603A CH311603DA CH311603A CH 311603 A CH311603 A CH 311603A CH 311603D A CH311603D A CH 311603DA CH 311603 A CH311603 A CH 311603A
Authority
CH
Switzerland
Prior art keywords
anilide
methyl
halogen
production
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 CH311603A publication Critical patent/CH311603A/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   Ilerstellung    eines neuen   basiseh substituierten Fettsaure- (2-halogen-6-    methyl-anilids), welches dadurch gekennzeichnet ist, da¯ man eine Verbindung der Formel
EMI1.1     
 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Dimethylamin umsetzt.



   Der Rest X kann in einem Halogenatom oder einem sonstigen für den   Austauseh    gegen den basischen Rest geeigneten   reaktionsfähi-    gen Substituenten, wie z. B. einer Alkylsul  fonyloxy-oder      Arylsulfonyloxygruppe,    bestehen. Der   Austallseh    der Gruppe X gegen den   Dimethylaminrest erfolgt z.    B. durch einfaches Erwärmen mit Dimethylamin   gege-    benenfalls in Gegenwart eines basisch reagierenden   Kondensationsmit. tels    oder von Dimethylamin im Überschuss.

   Das Dimethylaminoacet-(2-chlor-6-methyl-anilid) ist ein farbloses, unter 0, 2 mm Hg bei   128-130       sie-    dendes   öl,    das nach einiger Zeit zu farblosen, bei 71-73  schmelzenden Kristallen erstarrt.



  Das Hydrochlorid der Base schmilzt bei 231 bis   232  unter Zersetzung.   



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



     Beisnpiet    :
44 Gewichtsteile   Chloracet- (2-chlor-6-me-      thyl-anilid) (gewonnen dureh Umsetzen    von 2-Chlor-6-methyl-anilin mit Chloracetylchlorid in Gegenwart von Natriumacetat, Schmp. 140 bis 141 ) werden in 200 Gewichtsteilen Äthanol suspendiert und mit 81 Gewichtsteilen Dimethylamin versetzt. Die Temperatur steigt dabei leicht an n und ein   gober    Teil des Reak  tionsgemisehes geht    in   Losung.    Nun wird wÏhrend 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 Wasserdampf wird hierauf der Alkohol und das übersehüssige Dimethylamin abgeblasen und naeh dem Erkalten das zurüekbleibende   Ö1    in Äther aufgenommen. Nach dem Troeknen der Ïtherischen L¯sung und Verjagen des Lösungsmittels verbleibt ein   Öl,    das durch   Va. kullmdestillati, on    gereinigt wird. Man erhÏlt 43 Gewiehtsteile reines Dimethylamino  acet- (2-chlor-6-methyl-anilid),    was einer Ausbeute von 94% entspricht. Die Umsetzung mit Dimethylamin kann auch in Benzol stattfinden.



  



  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, is reacted with dimethylamine.



   The radical X can be in a halogen atom or another reactive substituent suitable for exchange with the basic radical, such as B. an alkyl sulfonyloxy or aryl sulfonyloxy group exist. The Austallseh of group X against the dimethylamine residue takes place z. B. by simply heating with dimethylamine, possibly in the presence of a basic condensation agent. means or of dimethylamine in excess.

   Dimethylaminoacet- (2-chloro-6-methyl-anilide) is a colorless oil that boils below 0.2 mm Hg at 128-130 and solidifies after some time to colorless crystals that melt at 71-73.



  The hydrochloride of the base melts at 231 to 232 with decomposition.



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



     Example:
44 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 200 parts by weight of ethanol and 81 parts by weight of dimethylamine 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 in a solution of the precipitate again. The alcohol and the excess dimethylamine 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 va. Kullmdestillati, on. 43 parts by weight of pure dimethylamino acet- (2-chloro-6-methyl-anilide) are obtained, which corresponds to a yield of 94%. The reaction with dimethylamine can also take place in benzene.

Claims (1)

PATENTANSPRUCH : Verfahren zur Herstellung eines neuen basisch substituierten FettsÏure-(2-halogen-6 methyl-anilids), dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI2.1 in welcher X einen reaktionsfähigen, während der Reaktion sich abspaltenden Rest bedeutet, mit Dimethylamin umsetzt. Das auf diese Weise erhaltene Dimethylaminoacet- (2-chlor- 6-methyl-anilid) bildet ein farbloses, unter 0, 2 mm Hg bei 128-130¯ siedendes Íl, das nach einiger Zeit zu farblosen, bei 71-73" schmelzenden Kristallen erstarrt. Das Hydroehlorid der Base schmilzt bei 231-232 unter Zersetzung. PATENT CLAIM: Process for the preparation of a new basic substituted FettsÏure- (2-halogen-6 methyl-anilids), characterized in that a compound of the formula EMI2.1 in which X is a reactive radical which is split off during the reaction, is reacted with dimethylamine. The dimethylaminoacet- (2-chloro-6-methyl-anilide) obtained in this way forms a colorless oil, boiling below 0.2 mm Hg at 128-130¯, which after some time turns into colorless crystals that melt at 71-73 " The hydrochloride of the base melts below at 231-232 Decomposition. Das neue Anilid soll als Lokalanästhetikum und als Zwischenprodukt Verwendung finden. The new anilide will be used as a local anesthetic and as an intermediate product. UNTERANSPRUCH : : Verfahren nach Patentanspruch, dadurch gekennzeichnet., dass man ein Ha] ogenacet-(2- chlor-6-methyl-anilid) mit Dimethylamin re agieren lϯt. SUBClaim:: Process according to claim, characterized in that a Ha] ogenacet- (2-chloro-6-methyl-anilide) is allowed to react with dimethylamine.
CH311603D 1952-02-25 1952-02-25 Process for the production of a new basic substituted fatty acid (2-halogen-6-methyl-anilide). CH311603A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH311603T 1952-02-25
CH307799T 1952-11-25

Publications (1)

Publication Number Publication Date
CH311603A true CH311603A (en) 1955-11-30

Family

ID=25735336

Family Applications (1)

Application Number Title Priority Date Filing Date
CH311603D CH311603A (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) CH311603A (en)

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