CH106124A - Process for the preparation of 4-chloro-1,2-thionaphthisatin. - Google Patents

Process for the preparation of 4-chloro-1,2-thionaphthisatin.

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Publication number
CH106124A
CH106124A CH106124DA CH106124A CH 106124 A CH106124 A CH 106124A CH 106124D A CH106124D A CH 106124DA CH 106124 A CH106124 A CH 106124A
Authority
CH
Switzerland
Prior art keywords
chloro
thionaphthisatin
preparation
parts
halogen
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 CH106124A publication Critical patent/CH106124A/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
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/58—[b]- or [c]-condensed
    • C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles

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

Description

  

      Verfahren    zur Herstellung des     4-Clilor-1,2-thionaphtliisatins.       Es wurde gefunden, dass man zu dem       4-Chlor-l,2-thionaphthisatin    gelangen kann,  wenn man im     4-Chlor-1,2-naphththioindoxyl,     durch Behandeln mit Halogen, die Wasser  stoffatome der     Methylengruppe    durch Ha  logen substituiert und hierauf die so er  haltenen Produkte mit verseifenden Mitteln,  wie anorganischen oder organischen Säuren,  behandelt, wobei die angelagerten Halogene  als     Igalogen-%,%,asserstoffsäuren        abgespalten     werden.  



  <I>Beispiel</I>  234,5 Teile     4-Chlor-1,2-naphththioiniioxyl     werden bei 30 bis 35   in 2500 Teilen Eis  essig suspendiert. Bei dieser Temperatur gibt  man unter     E.ühren    eine Lösung     von    820  Teilen Brom in 500 Teilen     Eisassig    zu. Es  entsteht eine braune Lösung; aus der sieh  bald ein gelbbrauner Niederschlag     abzu-          scheiden    beginnt:. Nach kurzem     Rühren    ist  das Brom verschwunden.

   Nach dem Filtrie  ren und     Umkristallisieren    des Niederschlages  aus heissem Eisessig erhält man das     2-1.)i-          bromid    des     4-Cfilor-1,2-thionaphtliisatins    in       W       guter Ausbeute als gelbe Kristalle vom  Schmelzpunkt 178  .  



  392,5 Teile     2-Dibromid    des     4-Chlor-.1,2-          thionaphthisatixis    werden nun in 7000     Teilen     85     %iger    Schwefelsäure suspendiert und un  ter Rühren auf 110   erhitzt.

   Unter     Broin-          wasserstoffabspaltung    geht der     Körper    mit  braunroter Farbe in     Lösung,    und     bzild    be  ginnt die     Abscheidung    des     4-Chlor-1,2-t.liio-          naphtliisatins.    Zur     Vervollständigung-    der       Bromwasserstoffabspaltung    wird einige Zeit  auf     120    bis 130   belassen, dann mit     Wasser     verdünnt, filtriert,

       genraschen    und     getrocknet.     Nach .dem     Umlösen    aus verdünnter Natron  lauge und     einmali(rem        Umkrlstalllsleren        alis     Benzol wird das     4-Clilor-l.,2-thionaphtliisaiin     in     violettroten    Nadeln     voni        Schmelzpunkt     <B><U>920'</U></B> erhalten.



      Process for the preparation of 4-Clilor-1,2-thionaphthiisatin. It has been found that the 4-chloro-l, 2-thionaphthisatin can be obtained if the hydrogen atoms of the methylene group are substituted by halogen in 4-chloro-1,2-naphththioindoxyl by treatment with halogen and then the Products obtained in this way are treated with saponifying agents such as inorganic or organic acids, with the accumulated halogens being split off as Igalogen -%,%, hydrogen acids.



  <I> Example </I> 234.5 parts of 4-chloro-1,2-naphththioiniioxyl are suspended at 30 to 35 in 2500 parts of glacial acetic acid. At this temperature, a solution of 820 parts of bromine in 500 parts of glacial acetic acid is added while stirring. A brown solution results; from which a yellow-brown precipitate soon begins to separate :. The bromine has disappeared after a brief stir.

   After filtration and recrystallization of the precipitate from hot glacial acetic acid, the 2-1.) I-bromide of 4-Cfilor-1,2-thionaphthiatisatin is obtained in good yield as yellow crystals with a melting point of 178.



  392.5 parts of 2-dibromide des 4-chloro-1,2-thionaphthisatixis are now suspended in 7000 parts of 85% strength sulfuric acid and heated to 110 with stirring.

   With splitting off of brine hydrogen, the body goes into solution with a brownish-red color, and the separation of 4-chloro-1,2-t.liionaphthiatisatin begins in bzild. To complete the elimination of hydrogen bromide, it is left at 120 to 130 for some time, then diluted with water, filtered,

       piqued and dried. After redissolving from dilute sodium hydroxide solution and one-time liquid crystal as benzene, the 4-chloro-1,2-thionaphthylic acid is obtained in violet-red needles with a melting point of <B><U>920'</U> </B>.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung des 4-Clilor-@ 1.?-tliionaplithisatins, dadurch gekennzeich net. dass man im 4-Clilor-1,2-naphththio-^ indoxyl, durch Behandeln mit Halogen, die Wasserstoffatome der Methylengruppe durch Halogen substituiert und hierauf die so er haltenen Produkte mit verseifenden Mitteln behandelt, wobei die angelagerten Halogene als Halogenwasserstoffsä.uren abgespalten werden. PATENT CLAIM: Process for the production of 4-Clilor- @ 1.?-tliionaplithisatins, thereby marked. that in 4-chloro-1,2-naphththio- ^ indoxyl, the hydrogen atoms of the methylene group are substituted by halogen by treatment with halogen, and the products thus obtained are then treated with saponifying agents, with the added halogens being split off as hydrogen halide acids .
CH106124D 1923-01-29 1923-02-12 Process for the preparation of 4-chloro-1,2-thionaphthisatin. CH106124A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH105234T 1923-01-29
CH106124T 1923-02-12

Publications (1)

Publication Number Publication Date
CH106124A true CH106124A (en) 1924-08-01

Family

ID=25706819

Family Applications (1)

Application Number Title Priority Date Filing Date
CH106124D CH106124A (en) 1923-01-29 1923-02-12 Process for the preparation of 4-chloro-1,2-thionaphthisatin.

Country Status (1)

Country Link
CH (1) CH106124A (en)

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