CH125475A - Process for the preparation of 5-methylisatin. - Google Patents

Process for the preparation of 5-methylisatin.

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Publication number
CH125475A
CH125475A CH125475DA CH125475A CH 125475 A CH125475 A CH 125475A CH 125475D A CH125475D A CH 125475DA CH 125475 A CH125475 A CH 125475A
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CH
Switzerland
Prior art keywords
methylisatin
preparation
toluenesulfo
parts
sodium
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH125475A publication Critical patent/CH125475A/en

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Description

  

  Verfahren zur Darstellung von     ä-lllethylisatin.       Es wurde gefunden, dass man     Isatine    oder  deren     N-Ai,ylsulfovei-biridungen    erhält, wenn       inan    auf Salze von     N-Ai-ylsulfoaniliden,    deren  Homologen, Derivaten und     Substitutionspro-          dukten    in Gegenwart indifferenter Verdün  nungsmittel     Oxalylchlorid    einwirken lässt und  die so erhältlichen     Oxaminsäurechloride    mit  sauren Kondensationsmitteln, wie Aluminium  chlorid, behandelt.

   Es entstehen so     N-Aryl-          sulfoverbindungen    der     Isatirie,        wohlcharalzteri-          sierte    Körper, die beim Behandeln mit     Ver-          seifungsmitteln,    zum Beispiel konzentrierte  Schwefelsäure, schon in der Kälte in die ent  sprechenden     Isatine    übergehen. Es gelingt so,       Isatirie    zu erhalten, die bisher nur schwierig  oder gar nicht zugänglich waren.  



  Gegenstand dieses Patentes ist ein Ver  fahren zur Darstellung von     5-iVIethylisatin,    da  durch gekennzeichnet, dass man     p-Toluolsulfo-          p-toluididnatrium    mit     Oxalylchlorid    umsetzt,  das gebildete     Oxaminsäurechlorid    durch Be  handlung mit sauren Kondensationsmitteln in  das     Stickstofftoluolsulfo-5-methylisatin    über  führt und dieses     zum        5-11lethylisatin    verseift.    Die Verbindung soll zur Herstellung von       Farbstoffen    und pharmazeutischen Produkten  Verwendung finden .  



  <I>Beispiel</I>  In das Gemisch von 200     Volumteilen          Schwefelkohlenstoff    und 14 Gewichtsteilen       Oxalylchlorid    werden unter Eiskühlung 28,3  Gewichtsteile,     p-Toluolsulfo-p-toluidnatrium     eingerührt und zur Vollendung der Umsetzung  einige Minuten zum Sieden erhitzt. In die  wieder mit Eis gekühlte Lösung werden 27  Gewichtsteile gepulvertes Aluminiumchlorid  eingetragen, innerhalb einer Viertelstunde zum  Sieden     erwärmt    und gekocht, bis die Chlor  wasserstoffentwicklung beendigt ist.  



  Das Reaktionsprodukt gibt man in eine  Mischung von etwa<B>560</B> Teilen Wasser  und 50     Volumteilen    konzentrierte Salzsäure:  destilliert den     Schwefelkohlenstoff    auf dem  Dampfbade ab, erhitzt einige Minuten zum  lebhaften Sieden und saugt das stark gelbe       N-p-toluolsulfo-5-methylisatin    ab. Zur Reini  gung kristallisiert man aus wenig Benzol oder  Eisessig um.

   Sm.     202-205",         Zur Überführung in das     5-Methylisatin     löst man die gepulverte Substanz in     konzen-          trierte    Schwefelsäure; worin sie     mitroterFarbe     löslich ist und giesst nach etwa eintägigem  Stehen in Wasser, wobei das bekannte 5  AIethylisatin     (Berl.    Berichte 40.266l, 4976  und 41.3034) vom 8m.182-184  rein ausfällt.



  Process for the preparation of ä-lllethylisatin. It has been found that isatins or their N-Ai, ylsulfovei-biridungen are obtained when salts of N-Ai-ylsulfoaniliden, their homologues, derivatives and substitution products in the presence of indifferent diluents, oxalyl chloride and the oxamic acid chlorides obtainable treated with acidic condensing agents such as aluminum chloride.

   The result is isatiric N-aryl sulfo compounds, well-charalted bodies which, when treated with saponifying agents, for example concentrated sulfuric acid, convert into the corresponding isatins even in the cold. In this way it is possible to preserve isatiry that was previously difficult or impossible to access.



  The subject of this patent is a process for the preparation of 5-iVIethylisatin, characterized in that p-toluenesulfo-p-toluidide sodium is reacted with oxalyl chloride, the oxamic acid chloride formed by treatment with acidic condensing agents in the nitrogen toluenesulfo-5-methylisatin leads and this saponified to 5-11lethylisatin. The compound is said to be used for the manufacture of dyes and pharmaceutical products.



  <I> Example </I> 28.3 parts by weight of sodium p-toluenesulfo-p-toluide are stirred into the mixture of 200 parts by volume of carbon disulfide and 14 parts by weight of oxalyl chloride and heated to boiling for a few minutes to complete the reaction. 27 parts by weight of powdered aluminum chloride are added to the solution, which is again cooled with ice, heated to boiling within a quarter of an hour and boiled until the evolution of hydrogen chloride has ceased.



  The reaction product is poured into a mixture of about <B> 560 </B> parts of water and 50 parts by volume of concentrated hydrochloric acid: the carbon disulfide is distilled off on the steam bath, heated to a lively boil for a few minutes and the bright yellow Np-toluenesulfo-5- methylisatin. For cleaning, recrystallize from a little benzene or glacial acetic acid.

   Sm. 202-205 ", To convert into 5-methylisatin, the powdered substance is dissolved in concentrated sulfuric acid; in which it is soluble with a red color and, after standing for about one day, it is poured into water, the well-known 5-methylisatin (Berl. Reports 40.266l , 4976 and 41.3034) from 8m 182-184 purely fails.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 5-Methyl- isatin, dadurch gekennzeichnet; dass man p-To- luolsulfo-p-toluididnatrium mit Oxalyleblorid umsetzt, das gebildete Oxaminsäure-Chlorid durch Behandlung mit sauren Kondensations mitteln in das Stickstoftoluolsulfo-5-methyl- isatin überführt und dieses zum 5-Metbylisatin verseift. PATENT CLAIM: Process for the preparation of 5-methyl isatin, characterized in that; that p-toluenesulfo-p-toluidide sodium is reacted with oxalylebloride, the oxamic acid chloride formed is converted into nitrogen toluenesulfo-5-methylisatin by treatment with acidic condensation agents and this is saponified to form 5-metbylisatin.
CH125475D 1926-01-28 1927-01-27 Process for the preparation of 5-methylisatin. CH125475A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE125475X 1926-01-28

Publications (1)

Publication Number Publication Date
CH125475A true CH125475A (en) 1928-04-16

Family

ID=5658685

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125475D CH125475A (en) 1926-01-28 1927-01-27 Process for the preparation of 5-methylisatin.

Country Status (1)

Country Link
CH (1) CH125475A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115260079A (en) * 2022-08-08 2022-11-01 湖北可赛化工有限公司 Synthetic method of isatin and derivatives thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115260079A (en) * 2022-08-08 2022-11-01 湖北可赛化工有限公司 Synthetic method of isatin and derivatives thereof

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