CH172951A - Process for the preparation of 5-chloro-7-methylisatin-a-chloride. - Google Patents

Process for the preparation of 5-chloro-7-methylisatin-a-chloride.

Info

Publication number
CH172951A
CH172951A CH172951DA CH172951A CH 172951 A CH172951 A CH 172951A CH 172951D A CH172951D A CH 172951DA CH 172951 A CH172951 A CH 172951A
Authority
CH
Switzerland
Prior art keywords
chloride
methylisatin
chloro
preparation
sep
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 CH172951A publication Critical patent/CH172951A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin

Landscapes

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

Description

  

  
EMI0001.0001     
  
    Verfahren <SEP> zur <SEP> hierstellung <SEP> von: <SEP> @-C.hlo@-i-meth@lisatin-c.-chlorid.       Es     wurde    gefunden. dass man das be  kannte     5-Chlor-7-methylisatin-a-chlorid    her  stellen kann, wenn     7-Methylisatin-a-chlorid          mit        im    Kerne chlorierenden Mitteln behan  delt wird. Die Behandlung des     7-Methylisa-          t:in-a-clilorids    mit den im Kerne     chlorieren-          den        Mitteln    kann in     verschiedenster    Weise.

    wie     zum    Beispiel in Gegenwart indifferenter       Lösungs-    oder Verdünnungsmittel; wie bei  spielsweise Benzol,     Chlorbenzol,    Nitrobenzol.       Tetracliloräthan    oder Chloroform erfolgen.  



  Als im Kerne chlorierende Mittel können       beispielsweise    Chlor oder     Sulfurylclilorid    in  Gegenwart oder Abwesenheit von     Haloge -          überträgern,    wie zum Beispiel .Tod.     Antimon-          pentachlorid    oder Eisen und dessen Salzelf  verwendet werden: besonders gute Resultate  in     betun    auf die Ausbeuten an     5-Chlor-ä-          methylisatin-a-chlorid    werden bei Verwen  dung von     Sulfurylchlorid    als     chlorierende     Mittel erhalten.  



  <I>Beispiel:</I>  16,1 Teile     7-IVIethylisatili    werden     durch          lialbstündio,es        Erwärmen    auf<B>80</B> bis 85       mil            -'?    Teilen     Phosphorpentachlorid    und 600 Tei  len Chlorbenzol in das     7-Methylisatin-a-chlo-          rid    übergeführt. Zu der auf etwa 50 bis 55  erkalteten Lösung werden unter Rühren     1.4     Teile     Sulfurylchlorid    gegeben. Hierauf wird  eine Stunde bei 6.0 bis 65   gehalten.

   Nach  dieser Zeit: ist die     Chlorierung,    die sich     unter     lebhafter     Scllwefeldioxydentwicklung    voll  zieht, beendet.  



  Wird das Lösungsmittel, zum Beispiel       durch        --#lidestillieren    im Vakuum,     grössten-          teils        entfernt.    so entsteht ein brauner Kri  stallbrei, der aus     5-Chlor-7-methylisatin-a-          chlorid        besteht:    durch     Abnutschen    und     Aus-          @\        ascheii        mit,    etwas     Petroläther    kann das     5-          Chlor-7-methylisatin-a-chlorid    isoliert wer  den.  



  In. vielen Fällen ist ein Isolieren des für       cLie        IT.erstellun'.    von Farbstoffen     wertvollen          :i-Chlor-7-lnetlivlisatin-a-chlorids        nicht    not  wendig: sondern es     kann.    ohne weiteres die  <U>Lösung</U> oder     Suspeilsloil    des     a-Chlorids    ver  wendet werden.     wie    dies beispielsweise bei  der     TZOnden        \ < ltion        finit    zur Herstellung indi-           goider    Farbstoffe     geeigneten    Komponenten  möglich ist.



  
EMI0001.0001
  
    Procedure <SEP> for <SEP> here <SEP> of: <SEP> @ -C.hlo @ -i-meth @ lisatin-c.-chloride. It was found. that the well-known 5-chloro-7-methylisatin-a-chloride can be produced if 7-methylisatin-a-chloride is treated with agents that are chlorinated in the nucleus. The treatment of the 7-methylate: in-a-clilorids with the agents chlorinating in the nucleus can be carried out in the most varied of ways.

    such as, for example, in the presence of inert solvents or diluents; such as for example benzene, chlorobenzene, nitrobenzene. Tetraclilorethane or chloroform take place.



  As a core chlorinating agent, for example, chlorine or sulfuryl chloride in the presence or absence of halogen - carriers, such as .Tod. Antimony pentachloride or iron and its salt elf are used: particularly good results in relation to the yields of 5-chloro-methylisatin-a-chloride are obtained when using sulfuryl chloride as the chlorinating agent.



  <I> Example: </I> 16.1 parts of 7-IVIethylisatili are made by lialbstündio, heating it to <B> 80 </B> to 85 mil - '? Parts of phosphorus pentachloride and 600 parts of chlorobenzene converted into 7-methylisatin a-chloride. 1.4 parts of sulfuryl chloride are added to the solution, which has cooled to about 50 to 55, with stirring. This is held at 6.0 to 65 for one hour.

   After this time: the chlorination, which takes place with vigorous evolution of sulfur dioxide, is over.



  If the solvent is largely removed, for example by - # lidistillation in a vacuum. The result is a brown crystal slurry consisting of 5-chloro-7-methylisatin-a-chloride: the 5-chloro-7-methylisatin-a-chloride can be isolated by suction filtration and extraction with a little petroleum ether .



  In. In many cases, it is necessary to isolate the IT. creation for cLie. valuable of dyes: i-chloro-7-netlivlisatin-a-chloride is not necessary: it can. the <U> solution </U> or suspeilsloil of the a-chloride can be used without further ado. as is possible, for example, with the TZOnden \ <ltion finite components suitable for the production of indigenous dyes.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung von 5-Chlor-7- methylisatin-a-chlorid, dadurch gekennzeich net, dass 7-Methylisatin-a-ehlorid mit im Kerne chlorierenden Mitteln behandelt wird. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass als im gerne chlo rierendes Mittel Sulfurvlchlorid verwendet wird. PATENT CLAIM Process for the production of 5-chloro-7-methylisatin-a-chloride, characterized in that 7-methylisatin-a-chloride is treated with agents that chlorinate the nucleus. SUBSTANTIAL CLAIM: A method according to the patent claim, characterized in that sulfur chloride is used as the preferred chlorinating agent.
CH172951D 1933-04-08 1933-04-08 Process for the preparation of 5-chloro-7-methylisatin-a-chloride. CH172951A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH172951T 1933-04-08
CH169349T 1933-04-08

Publications (1)

Publication Number Publication Date
CH172951A true CH172951A (en) 1934-10-31

Family

ID=25718704

Family Applications (1)

Application Number Title Priority Date Filing Date
CH172951D CH172951A (en) 1933-04-08 1933-04-08 Process for the preparation of 5-chloro-7-methylisatin-a-chloride.

Country Status (1)

Country Link
CH (1) CH172951A (en)

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