CH104471A - Process for the preparation of a new pyrazolone derivative. - Google Patents

Process for the preparation of a new pyrazolone derivative.

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Publication number
CH104471A
CH104471A CH104471DA CH104471A CH 104471 A CH104471 A CH 104471A CH 104471D A CH104471D A CH 104471DA CH 104471 A CH104471 A CH 104471A
Authority
CH
Switzerland
Prior art keywords
hot water
difficult
new
parts
sulfamido
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 CH104471A publication Critical patent/CH104471A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • C07D231/24—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms having sulfone or sulfonic acid radicals in the molecule

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Pyr        azolonderirates.            Ewurde    gefunden, dass sich das     2-To-          luidin--l-sulfamid    durch     Diazotieren    und hier  auf durch Reduzieren der     Diazoverbindung     in das     3-Sulfaniido-6-methylphenylhydrazin     überführen lässt, welches mit     Oxalessigester     zur     1-(3'-Sulfamido-6'-methyl)-phenyl-5-py-          razolon-3-karbonsäure    kondensiert werden  kann. Diese ist ein wertvoller Ausgangsstoff  zur Herstellung von Farbstoffen.  



  <I>Beispiel:</I>  20,7 Gewichtsteile     2-Toluidin-4-sulfa.mid,     in 25 Teilen Wasser und 12 Teilen konzen  trierter Salzsäure gelöst, werden mit 16 Tei  len konzentrierter Salzsäure versetzt und mit  Eis und 7 Teilen Nitrit bei 0       dia.zotiert.    Die       Diazolösung    giesst man zu einer auf<B>10'</B> ge  kühlten wässerigen     Sulfitlösung,    hergestellt  aus 25 Teilen     Natriumbisulfit    und 20 Teilen  konzentrierter Natronlauge. Die erst gelbe,  bald fast farblos werdende Lösung wird bis  zur beginnenden     Kristallisation    eingedampft  und noch heiss mit 25 Teilen konzentrierter  Salzsäure versetzt.

   Nach dem Abtreiben der  schwefligen Säure überlässt man die Lösung    der Kristallisation, wobei sich in guter Aus  beute das     3-Sulfamido-6-methylphenylhydra-          zin    abscheidet.  



  Die durch Filtration abgeschiedene     Hy-          drazinverbindung    wird in einem geeigneten  Lösungsmittel, beispielsweise in 150 Teilen  Alkohol, gelöst und bei fortwährend eben  kongosauer gehaltener Reaktion mit 16 bis  18 Teilen     Oxalessigester    kondensiert. Die       Kondensation    kann auch in Wasser ausge  führt werden.

   Man versetzt nun mit 150 Tei  len Wasser, gibt nach und nach bei gewöhn  licher     Temperatur    Natronlauge zu bis zur  bleibenden, kräftig     phenolphtaleinalkalis@chen     Reaktion, destilliert .den Alkohol ab und  fällt die     1.-(3'-Sulfamido-6'-methyl)-phenyl-          5-pyra.zolon-3-karbonsäure    mit .Salzsäure aus.  Sie kann durch     Umkristallisieren    aus heissem  Wasser gereinigt werden und stellt     dann    fast       weisse        Kristalle    dar, welche bei etwa 169    unter Aufschäumen schmelzen, dann wieder  fest werden, um bei etwa 225   erneut unter  Bräunung und     Aufs,ehäumen    zu schmelzen.

         Kristallisiert    .man sie .aus Eisessig, so erhält  man sie direkt bei etwa 225   schmelzend.      Sie ist in kaltem Wasser sehr schwer, in.       heissem    ziemlich schwer, in Eisessig kalt  schwer, heiss leicht, in     Alkalien    leicht löslich.



  Process for the production of a new Pyr azolonderirates. It has been found that 2-toluidine-1-sulfamide can be converted into 3-sulfaniido-6-methylphenylhydrazine by diazotizing and here by reducing the diazo compound, which with oxaloacetic ester gives 1- (3'-sulfamido-6 '-methyl) -phenyl-5-py- razolon-3-carboxylic acid can be condensed. This is a valuable raw material for the production of dyes.



  <I> Example: </I> 20.7 parts by weight of 2-toluidine-4-sulfa.mid, dissolved in 25 parts of water and 12 parts of concentrated hydrochloric acid, are mixed with 16 parts of concentrated hydrochloric acid and mixed with ice and 7 parts of nitrite dia. quoted at 0. The diazo solution is poured into an aqueous sulfite solution, cooled to <B> 10 '</B>, prepared from 25 parts of sodium bisulfite and 20 parts of concentrated sodium hydroxide solution. The solution, which is yellow at first and soon becomes almost colorless, is evaporated until crystallization begins and 25 parts of concentrated hydrochloric acid are added while it is still hot.

   After the sulphurous acid has been driven off, the solution is left to crystallize, in which case the 3-sulfamido-6-methylphenylhydrazine is deposited in good yield.



  The hydrazine compound separated off by filtration is dissolved in a suitable solvent, for example in 150 parts of alcohol, and condensed with 16 to 18 parts of oxaloacetic ester while the reaction is continuously kept acidic in the Congo. The condensation can also be carried out in water.

   150 parts of water are then added, sodium hydroxide solution is gradually added at the usual temperature until the strong phenolphthalein-alkaline reaction remains, the alcohol is distilled off and the 1 .- (3'-sulfamido-6'-methyl ) -phenyl-5-pyra.zolon-3-carboxylic acid with hydrochloric acid. It can be purified by recrystallization from hot water and then represents almost white crystals, which melt with foaming at about 169, then solidify again, only to melt again at about 225 with browning and puffing up.

         If you crystallize it from glacial acetic acid, you get it melting directly at about 225. It is very difficult in cold water, quite difficult in hot water, difficult in cold glacial acetic acid, easy in hot water, easily soluble in alkalis.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Pyrazolonderivates, dadurch gekennzeichnet, dass man das 2-Toluidin-4-sulfamid durch Diazotieren und hierauf durch Reduzieren der Diazoverbindung in das 3-Sulf amido-6- methylphenylhydrazin überführt und diese mit Oxalessigester kondensiert. Die neue 1-(3' - Sulfamido-6'-methyl) PATENT CLAIM: Process for the production of a new pyrazolone derivative, characterized in that the 2-toluidine-4-sulfamide is converted into the 3-sulfamido-6-methylphenylhydrazine by diazotization and then by reducing the diazo compound and this is condensed with oxaloacetate. The new 1- (3'-sulfamido-6'-methyl) -pheny 1-5-py ra zo- lon-3-harbo.nsä,ure, bildet fast weisse Kri stalle, welche aus heissem Wasser kristalli siert., bei etwa, 169 unter Aufschäumen Schmelzen, dann wieder fest werden, um bei etwa. 225 erneut unter Bräunung und Auf schäumen zu schmelzen. -pheny 1-5-py ra zolon-3-harbo.nsä, ure, forms almost white crystals, which crystallize from hot water., melt at about .169 with foaming, then solidify again at about . 225 to melt again with browning and frothing. Kristallisiert man sie aus Eisessig, so erhält man sie direkt bei etwa. 225 schmelzend. Sie ist in kaltem Wasser sehr schwer, in heissem ziemlich schwer, in Eisessig kalt schwer, heiss leicht, in Alkalien leicht löslich. If you crystallize them from glacial acetic acid, you get them directly at about. 225 melting. It is very difficult in cold water, quite difficult in hot water, difficult in cold glacial acetic acid, easy in hot water, easily soluble in alkalis.
CH104471D 1922-11-11 1922-12-01 Process for the preparation of a new pyrazolone derivative. CH104471A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH102277T 1922-11-11
CH104471T 1922-12-01

Publications (1)

Publication Number Publication Date
CH104471A true CH104471A (en) 1924-04-16

Family

ID=25706155

Family Applications (1)

Application Number Title Priority Date Filing Date
CH104471D CH104471A (en) 1922-11-11 1922-12-01 Process for the preparation of a new pyrazolone derivative.

Country Status (1)

Country Link
CH (1) CH104471A (en)

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