CH199647A - Process for the preparation of thiazole-4,5-dicarboxylic acid. - Google Patents

Process for the preparation of thiazole-4,5-dicarboxylic acid.

Info

Publication number
CH199647A
CH199647A CH199647DA CH199647A CH 199647 A CH199647 A CH 199647A CH 199647D A CH199647D A CH 199647DA CH 199647 A CH199647 A CH 199647A
Authority
CH
Switzerland
Prior art keywords
sep
thiazole
dicarboxylic acid
preparation
acid
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH199647A publication Critical patent/CH199647A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

      Verfahren    zur Herstellung von     Thiazol-4,6-diearbonsäure.            Gegenstand    der     vorliegenden        Erfindung     ist ein     Verfahren    zur     Herstellung    von     T.hi-          azol-4,;

  5-idiearbonsäure,        welches    dadurch ge  kennzeichnet     ist,        dass    man     Thioformamid     auf einen     Ilaloigenoxalessigs-äureester    einwir  ken     lässt        und    die     entstandene    Verbindung       verseift.     



  Die so     gewonnene        Thiazol-4,5-di,carbon-          säure    bildet Kristalle vom     Zersetzungspunkt     177  .  



  Die neue Verbindung soll     als        Zwischen-          pr2dukt    zur Herstellung     pharmazeutisch     wirksamer     Verbindungen    dienen.  



       Beispiel:     Man     lä-sst    6 Teile     Thiaformamid    und 22  Teile     Chloroxalessigsäurediäthylester    in Ge  genwart oder     Abwesenheit    eines Lösungs  mittels     miteinander        bis        zur    beendeten Um  setzung     reagieren,        entfernt    gegebenenfalls  das     Lösungsmittel    und     reinigt    den entstan  denen     Th@iazol-4,

  5-@dicarbonsäurediäthylester     durch Destillation     im        Vakuum.    Er siedet bei  175   unter<U>12</U> mm     Druck.    Der Ester wird  Hierauf mit     alkoholischer    Natronlauge ver-  
EMI0001.0045     
  
    seift. <SEP> Die <SEP> so <SEP> gewonnene <SEP> Tliiazol-4,5=dicarbon  säure <SEP> zeigt,den <SEP> Zemeetzungspunkt <SEP> von <SEP> 177 <SEP>  .
<tb>  



  Durch <SEP> Koch-en <SEP> mit <SEP> Essigsäureaa@hydrid
<tb>  wird <SEP> :die <SEP> sich <SEP> in <SEP> 4"Stellung <SEP> befindliche
<tb>  Carboxyl,grupp,e <SEP> abgespalten <SEP> und <SEP> man <SEP> erhält
<tb>  Thiazol-5-carbo,nsäure <SEP> vom <SEP> F. <SEP> 19,6 <SEP> bis <SEP> 197 <SEP>  
<tb>  (k<B>(U</B>r.).
<tb>  



  .Statt <SEP> Chloroxalessigsäurediäthylester <SEP> kann
<tb>  auch <SEP> ein <SEP> anderer <SEP> Halogenoxalessigsäureester
<tb>  Verwendung <SEP> finden.



      Process for the preparation of thiazole-4,6-diacid. The present invention relates to a process for the preparation of T.hi- azol-4;

  5-idiearboxylic acid, which is characterized in that thioformamide is allowed to act on an Ilaloigenoxalessigsäureester and the resulting compound is saponified.



  The thiazole-4,5-di-carboxylic acid obtained in this way forms crystals with a decomposition point of 177.



  The new compound is intended to serve as an intermediate for the manufacture of pharmaceutically active compounds.



       Example: 6 parts of thiaformamide and 22 parts of chloroxalacetic acid diethyl ester are allowed to react with one another in the presence or absence of a solvent until the reaction is complete, the solvent is removed if necessary and the thiazole-4 formed is purified.

  5- @ dicarboxylic acid diethyl ester by distillation in vacuo. It boils at 175 under <U> 12 </U> mm of pressure. The ester is then treated with alcoholic caustic soda
EMI0001.0045
  
    soaps. <SEP> The <SEP> thus <SEP> obtained <SEP> Tliiazole-4,5 = dicarboxylic acid <SEP> shows the <SEP> decomposition point <SEP> of <SEP> 177 <SEP>.
<tb>



  By <SEP> cooking <SEP> with <SEP> acetic acid aa @ hydrid
<tb> becomes <SEP>: <SEP> is <SEP> in <SEP> 4 "position <SEP>
<tb> carboxyl, group, e <SEP> split off <SEP> and <SEP> you get <SEP>
<tb> Thiazole-5-carbonic acid <SEP> from <SEP> F. <SEP> 19.6 <SEP> to <SEP> 197 <SEP>
<tb> (k <B> (U </B> r.).
<tb>



  Instead of <SEP> chloroxaloacetic acid diethyl ester <SEP> can
<tb> also <SEP> a <SEP> other <SEP> halooxaloacetic acid ester
<tb> Find use <SEP>.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Thiazo1- 4"5-dicarbonsäure,dadurch gekennzeichnet, dass man Thioformamid auf einen Halogen- oxalessgsiäureestereinwirken lässt und :die entstandene Verbindung verseift. Die so gewonnene Thiazol-4,5-dicarbon- säuTe bildet Kristalle vom Zersetzungspunkt 177 . PATENT CLAIM: Process for the production of thiazo1-4 "5-dicarboxylic acid, characterized in that thioformamide is allowed to act on a halooxalessgic acid ester and: the resulting compound is saponified. The thiazole-4,5-dicarboxylic acid obtained in this way forms crystals with a decomposition point of 177 . Die neue Verbindung soll als Zwischen- produkt zur Herstellung pharmazeutisch wirksamer Verbindungen dienen. The new compound is intended to serve as an intermediate for the production of pharmaceutically active compounds.
CH199647D 1936-06-20 1936-06-20 Process for the preparation of thiazole-4,5-dicarboxylic acid. CH199647A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH192849T 1936-06-20
CH199647T 1936-06-20

Publications (1)

Publication Number Publication Date
CH199647A true CH199647A (en) 1938-08-31

Family

ID=25722326

Family Applications (1)

Application Number Title Priority Date Filing Date
CH199647D CH199647A (en) 1936-06-20 1936-06-20 Process for the preparation of thiazole-4,5-dicarboxylic acid.

Country Status (1)

Country Link
CH (1) CH199647A (en)

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