CH205063A - Process for the preparation of terephthaloyl-1-anilide-4-chloride. - Google Patents

Process for the preparation of terephthaloyl-1-anilide-4-chloride.

Info

Publication number
CH205063A
CH205063A CH205063DA CH205063A CH 205063 A CH205063 A CH 205063A CH 205063D A CH205063D A CH 205063DA CH 205063 A CH205063 A CH 205063A
Authority
CH
Switzerland
Prior art keywords
terephthaloyl
anilide
chloride
aniline
mole
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH205063A publication Critical patent/CH205063A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • 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
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur Herstellung von     Terephtbaloyl-I-anilüd-4-chlorid.       Gegenstand des vorliegenden Zusatzpaten  tes ist ein Verfahren zur Herstellung von       Terephthaloyl-l-anilid-4-chlorid,    welches da  durch gekennzeichnet ist, dass man auf ein       Mol        Terephthaloylchlorid    in Gegenwart von  organischen Lösungsmitteln, die nicht mit  den     Säurehalogenidgruppen    reagieren, ein     Mol     Anilin in Form seines mineralsauren Salzes  einwirken     lässt:

       Die so erhaltene, bisher nicht bekannte  Verbindung soll als Zwischenprodukt für die  Herstellung von     Farbstoffen,    pharmazeutischen  Produkten und Textilhilfsmitteln Verwendung  finden.  



  <I>Beispiel:</I>  In eine Lösung von 112 Gewichtsteilen       Terephthaloylchlorid    in 600     Volumteileti    Ace  ton werden bei 50 bis 55 o C 65 Gewichtsteile  salzsaures Anilin eingetragen; das     Anilinsalz     geht allmählich in Lösung. Nach beendetem  Eintragen wird das Reaktionsgemisch so lange    zum Sieden erhitzt, bis das in geringen Men  gen gebildete     Terepbthaloyldianilid    sich aus  zuscheiden beginnt. Hierauf wird sofort  filtriert und durch starkes Abkühlen das       Terephthaloyl-l-anilid-4-chlorid    der Formel  
EMI0001.0015     
    abgeschieden. Das abgesaugte und mit kaltem  Aceton gewaschene Produkt wird im Vakuum  bei Zimmertemperatur getrocknet.

   Durch Ein  engen der Mutterlauge und anschliessendes  Abkühlen werden weitere Mengen der Ver  bindung erhalten. Die Ausbeute beträgt 90  bis 95     0%    der Theorie (bezogen auf salzsaures  Anilin.  



  An Stelle von Aceton als Lösungsmittel  können andere     Ketone,    wie     Methyläthylketon     oder     Diäthylketon,    sowie     Kohlenwasserstoffe,     wie Benzol und     gylol,    allein oder in Mi  schung mit den bereits erwähnten Betonen,  ferner auch     Dioxan    verwendet werden.      Die erhaltene, bisher nicht bekannte Ver  bindung bildet farblose Kristalle, die bei 274  bis 275   C schmelzen. Sie reagiert zum  Beispiel energisch mit Anilin unter Bildung  des     Terephthaloyldianilida    vom Schmelzpunkt  336   C.



      Process for the production of terephthalic-1-anilide-4-chloride. The subject of the present Zusatzpaten tes is a process for the preparation of terephthaloyl-l-anilide-4-chloride, which is characterized by the fact that one mole of aniline in one mole of terephthaloyl chloride in the presence of organic solvents that do not react with the acid halide groups The form of its mineral acid salt can act:

       The previously unknown compound obtained in this way is intended to be used as an intermediate for the production of dyes, pharmaceutical products and textile auxiliaries.



  <I> Example: </I> 65 parts by weight of hydrochloric aniline are added to a solution of 112 parts by weight of terephthaloyl chloride in 600 parts by volume of acetone at 50 to 55 o C; the aniline salt gradually goes into solution. After the end of the introduction, the reaction mixture is heated to the boil until the small amounts of terepbthaloyldianilide formed begins to separate out. It is then filtered immediately and the terephthaloyl-1-anilide-4-chloride of the formula by vigorous cooling
EMI0001.0015
    deposited. The product which has been filtered off with suction and washed with cold acetone is dried in vacuo at room temperature.

   By narrowing the mother liquor and then cooling it, further amounts of the compound are obtained. The yield is 90 to 95% of theory (based on hydrochloric aniline.



  Instead of acetone as a solvent, other ketones, such as methyl ethyl ketone or diethyl ketone, and hydrocarbons such as benzene and gylene, alone or in admixture with the concretes already mentioned, and also dioxane can be used. The previously unknown compound obtained forms colorless crystals that melt at 274 to 275 C. For example, it reacts vigorously with aniline to form terephthaloyldianilida with a melting point of 336 C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Tereph- thaloyl-l-anilid-4-ehlorid, dadurch gekenn zeichnet, dass man auf ein Mol Terephthaloyl- chlorid in Gegenwart von organischen Lö sungsmitteln, die nicht mit den Säure halogenidgruppen reagieren, ein Mol Anilin in Form seines mineralsauren Salzes ein wirken lässt. Die so erhaltene, bisher nicht bekannte Verbindung bildet farblose Kristalle, die bei 274 bis 275 C schmelzen. Sie reagieren zuni Beispiel energisch mit Anilin unter Bildung des Terephthaloyldianilids vom Schmelzpunkt 336 C. PATENT CLAIM: A process for the production of terephthaloyl-l-anilide-4-ehlorid, characterized in that one mole of aniline in the form of one mole of terephthaloyl chloride in the presence of organic solvents that do not react with the acid halide groups its mineral acid salt can act. The previously unknown compound obtained in this way forms colorless crystals which melt at 274 to 275 C. For example, they react vigorously with aniline to form terephthaloyldianilide with a melting point of 336 C. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man Aceton als Lö sungsmittel verwendet. SUBClaim: Method according to claim, characterized in that acetone is used as the solvent.
CH205063D 1936-12-23 1937-12-13 Process for the preparation of terephthaloyl-1-anilide-4-chloride. CH205063A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE205063X 1936-12-23
CH201953T 1937-12-13

Publications (1)

Publication Number Publication Date
CH205063A true CH205063A (en) 1939-05-31

Family

ID=25723754

Family Applications (1)

Application Number Title Priority Date Filing Date
CH205063D CH205063A (en) 1936-12-23 1937-12-13 Process for the preparation of terephthaloyl-1-anilide-4-chloride.

Country Status (1)

Country Link
CH (1) CH205063A (en)

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