CH282935A - Process for the preparation of an acylating agent. - Google Patents

Process for the preparation of an acylating agent.

Info

Publication number
CH282935A
CH282935A CH282935DA CH282935A CH 282935 A CH282935 A CH 282935A CH 282935D A CH282935D A CH 282935DA CH 282935 A CH282935 A CH 282935A
Authority
CH
Switzerland
Prior art keywords
acylating agent
sodium
pyridine
preparation
groups
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH282935A publication Critical patent/CH282935A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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

Description

  

  Verfahren zur Herstellung eines     Acylierungsmittels.       Es wurde gefunden,     da.ss        inan    ein wertvol  les     Acylierungsmittel    erhält, wenn man     furan-          2-carbonsäure-5-sulfonsaures    Natrium in Ge  genwart eines Überschusses an     Pyridin        finit          Phosgen    behandelt.  



  Das erhaltene neue     Acylierungsmittel    ist  eine dunkelbraune, nicht gelöstes Natrium  chlorid und     Pyridinehlorhydrat    enthaltende  Lösung, die sich zur     Acylierung    der verschie  densten -NN-Gruppen und -GH-Gruppen  enthaltenden Verbindungen, z. B. von     Azo-          farbstoffen,    eignet und die     Einführung    von  Resten der Formel  
EMI0001.0016     
    in solchen Verbindungen ermöglicht.  



  Das als Ausgangsstoff verwendbare     furan-          2-carbonsäure-5-sulfonsaure    Natrium kann  zum Beispiel nach der im      American        Chemical          .lournal     10, 373 (1888) durch     Hill    und Pal  men angegebenen Methode hergestellt werden.  



       Pyridin    muss beim vorliegenden Verfahren  im     1.'berscliuss    vorhanden sein, das heisst es  muss mehr     Pyridin    vorhanden sein, als zur       Absättigung    sämtlicher im     Reaktionsgemiseh     anwesender Säuregruppen erforderlich ist.  



  Zweckmässig wird das     furan-2-earbonsäure-          5-sulfonsaure    Natrium in     Pyridin    eingetragen  und hierauf bei einer etwas erhöhten Tempera  tur, z. B. bei 30 bis 40 , gasförmiges     Phosgen     eingeleitet..

      <I>Beispiel:</I>  18,6 Teile     kristallwasserfreies        2-furancar-          bonsäure-5-sulfonsatires    Natrium         (C5H306SNa:       dargestellt nach     Hill        Lind        Palmer,        American          Chemical    Journal, 10, 373 [l.888]) werden in  120     Volumteilen    trockenem     Pyridin    bei 70 bis  75  unter Rühren vermischt. Zum erhaltenen  Gemisch lässt man bei gewöhnlicher Tempera  tur 8,6 Teile gasförmiges     Phosgen    innert etwa       l1/,2    Stunden einströmen.



  Process for the preparation of an acylating agent. It has been found that a valuable acylating agent is obtained if sodium furan-2-carboxylic acid-5-sulfonic acid is treated with finite phosgene in the presence of an excess of pyridine.



  The obtained new acylating agent is a dark brown, undissolved sodium chloride and pyridine chlorohydrate containing solution, which is used to acylate the most diverse -NN groups and -GH groups-containing compounds such. B. of azo dyes, is suitable and the introduction of residues of the formula
EMI0001.0016
    enabled in such connections.



  The sodium furan-2-carboxylic acid-5-sulfonic acid which can be used as the starting material can be prepared, for example, by the method given by Hill and Palmen in American Chemical.



       In the present process, pyridine must be present in the first excess, i.e. more pyridine must be present than is necessary to saturate all of the acid groups present in the reaction mixture.



  The furan-2-carboxylic acid-5-sulfonic acid sodium is expediently entered into pyridine and then at a slightly elevated tempera ture, e.g. B. at 30 to 40, introduced gaseous phosgene ..

      <I> Example: </I> 18.6 parts of anhydrous 2-furancarboxylic acid-5-sulfonsatires sodium (C5H306SNa: prepared according to Hill Lind Palmer, American Chemical Journal, 10, 373 [1888]) are in 120 parts by volume dry pyridine at 70 to 75 mixed with stirring. To the mixture obtained, 8.6 parts of gaseous phosgene are allowed to flow in at an ordinary temperature within about 11/2 hours.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Acylie- rungsmittels, dadurch gekennzeichnet, dass man furan-2-carbonsä.ure-5-sulfonsaures Na trium in Gegenwart eines Überschusses an Py- ridin mit Phosgen behandelt. Claim: Process for the production of an acylating agent, characterized in that sodium furan-2-carboxylic acid-5-sulfonic acid is treated with phosgene in the presence of an excess of pyridine. Das erhaltene neue Aeylierungsmittel ist eine dunkelbraune, nicht gelöstes Natrium- ehlorid und Py ridinehlorhydrat enthaltende Lösung, die sich zur Acylierung der verschie densten -NN-Gruppen Lind -ON-Gruppen enthaltenden Verbindungen, z. B. von Azofar- stoffen, eignet und die Einführung von Resten CIPP Formel EMI0001.0061 in solchen Verbindungen ermöglicht. The new Aeylierungsmittel obtained is a dark brown, undissolved sodium ehlorid and Pyridinehlorhydrat containing solution, which is used to acylate the most diverse -NN groups and -ON groups containing compounds, eg. B. of azo fars, is suitable and the introduction of residues CIPP formula EMI0001.0061 enabled in such connections.
CH282935D 1949-07-22 1949-07-22 Process for the preparation of an acylating agent. CH282935A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH282935T 1949-07-22
CH276416T 1949-07-22

Publications (1)

Publication Number Publication Date
CH282935A true CH282935A (en) 1952-05-15

Family

ID=25731692

Family Applications (1)

Application Number Title Priority Date Filing Date
CH282935D CH282935A (en) 1949-07-22 1949-07-22 Process for the preparation of an acylating agent.

Country Status (1)

Country Link
CH (1) CH282935A (en)

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