CH282936A - Process for the preparation of an acylating agent. - Google Patents

Process for the preparation of an acylating agent.

Info

Publication number
CH282936A
CH282936A CH282936DA CH282936A CH 282936 A CH282936 A CH 282936A CH 282936D A CH282936D A CH 282936DA CH 282936 A CH282936 A CH 282936A
Authority
CH
Switzerland
Prior art keywords
pyridine
acylating agent
preparation
furan
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 CH282936A publication Critical patent/CH282936A/en

Links

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)

Description

  

  Verfahren zur Herstellung eines     Acylierungsmittels.       Es wurde gefunden, dass man ein wertvol  les     Aeylierungsmittel    erhält, wenn man     Furan-          2-carbonsäure-5-sulfonsäure    in Gegenwart  eines Überschusses an     Pyridin    mit     Phosgen     behandelt.  



  Das erhaltene neue     Acylierungsmittel    ist  eine dunkelbraune, nicht gelöstes     Pyridin-          chlorhydrat    enthaltende Lösung, die sich zur       Acylierung    der verschiedensten     -NH-Grup-          pen    und     -OH-Gruppen    enthaltenden Verbin  dungen, z. B. von     Azofarbstoffen,    eignet und  die Einführung von Resten der Formel  
EMI0001.0015     
    in solchen Verbindungen ermöglicht..  



  Die als Ausgangsstoff verwendbare     Furan-          2-earbonsä.ure-5-sulfonsäure    kann zum Beispiel  durch Umsetzung von     Furan-2-carbonsäure     mit     Schwefeltr        ioxy        cl    in flüssigem Schwefel  dioxyd hergestellt werden.  



       Pyridin    muss beim vorliegenden Verfahren  im     Überschuss    vorhanden sein, das heisst es  muss mehr     Pyridin    vorhanden sein, als zur       Absättigung        sämtlicher    im Reaktionsgemisch  anwesender Säuregruppen erforderlich ist.  



  Zweckmässig wird die     Furan-2-carbon-          säure-5-sulfonsäux-e    in     Pyridin    eingetragen    Lind hierauf bei einer etwas erhöhten Tem  peratur, z. B. bei 30 bis 40 , gasförmiges     Phos-          gen    allmählich eingeleitet.  



  <I>Beispiel:</I>  19,2 Teile     Furan-2-carbonsäure-5-sulfon-          säure    werden in 90     Volumteilen    trockenem       Pyridin    unter Rühren gelöst. Zu der erhal  tenen Lösung werden dann 11,9 Teile     Phosgen     bei 30 bis 40  innert etwa 2 Stunden einge  leitet.



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



  The new acylating agent obtained is a dark brown, undissolved pyridine chlorohydrate-containing solution, which is used for acylating a wide variety of -NH groups and -OH groups-containing compounds, eg. B. of azo dyes, and the introduction of residues of the formula
EMI0001.0015
    allows in such connections ..



  The furan-2-carboxylic acid 5-sulfonic acid which can be used as a starting material can be prepared, for example, by reacting furan-2-carboxylic acid with sulfur trioxy cl in liquid sulfur dioxide.



       In the present process, pyridine must be present in excess, that is to say more pyridine has to be present than is necessary to saturate all of the acid groups present in the reaction mixture.



  The furan-2-carboxylic acid-5-sulfonsäux-e is expediently entered in pyridine and then at a slightly elevated temperature, e.g. B. at 30 to 40, gaseous phosgene gradually introduced.



  <I> Example: </I> 19.2 parts of furan-2-carboxylic acid-5-sulfonic acid are dissolved in 90 parts by volume of dry pyridine with stirring. To the obtained solution 11.9 parts of phosgene are then passed at 30 to 40 within about 2 hours.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Acylie- rungsmittels, dadurch gekennzeichnet, dass man Furan-2-carbonsäur e-5-sulfonsäure in Ge genwart eines Überschusses an Pyridin mit Phosgen behandelt. PATENT CLAIM: Process for the production of an acylating agent, characterized in that furan-2-carboxylic acid e-5-sulfonic acid is treated with phosgene in the presence of an excess of pyridine. Das erhaltene neue Aey lierungsmittel ist eine dunkelbraune, nicht gelöstes Pyridin- chlorhydrat enthaltende Lösung, die sich zur Aeylierung der verschiedensten -NH-Grup- pen und -OH-Gruppen enthaltenden Verbin dungen, z. B. von Azofarbstoffen, eignet. und die Einführung von Resten der Formel EMI0001.0052 in solchen Verbindungen ermöglicht. The new Aey lierungsmittel obtained is a dark brown, undissolved pyridine chlorohydrate containing solution, which are used for the aylation of various -NH groups and -OH groups containing compounds, z. B. of azo dyes is suitable. and the introduction of remnants of the formula EMI0001.0052 enabled in such connections.
CH282936D 1949-07-22 1949-07-22 Process for the preparation of an acylating agent. CH282936A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH282936T 1949-07-22
CH276416T 1949-07-22

Publications (1)

Publication Number Publication Date
CH282936A true CH282936A (en) 1952-05-15

Family

ID=25731693

Family Applications (1)

Application Number Title Priority Date Filing Date
CH282936D CH282936A (en) 1949-07-22 1949-07-22 Process for the preparation of an acylating agent.

Country Status (1)

Country Link
CH (1) CH282936A (en)

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