CH119718A - Process for the preparation of the 1- (4'-sulfophenyl) -5-pyrazolone-3-carboxylic acid ethyl ester. - Google Patents

Process for the preparation of the 1- (4'-sulfophenyl) -5-pyrazolone-3-carboxylic acid ethyl ester.

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Publication number
CH119718A
CH119718A CH119718DA CH119718A CH 119718 A CH119718 A CH 119718A CH 119718D A CH119718D A CH 119718DA CH 119718 A CH119718 A CH 119718A
Authority
CH
Switzerland
Prior art keywords
ethyl ester
preparation
carboxylic acid
sulfophenyl
acid ethyl
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 CH119718A publication Critical patent/CH119718A/en

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Description

  

  Verfahren zur Darstellung des     1-(9-Stilfophonyl)-5-pyrazi)loii-3-karbonsilureätliylesters.       Es ist gefunden worden,     dass    man die  Ester der     Sulfop#,riizolonlzarbonsäure    von  folgender Zusammensetzung:

    
EMI0001.0004     
    worin R einen     AlkYlrest    und X einen aro  matischen Kern, seine Homologen und     Sub-          stitutionsprodukte    bedeutet, in der Weise  herstellen kann,     dass    man die Hydrazone aus  den entsprechenden     X-Hydrazinsulfosäureii     (X wie oben) und     Oxalessigester    kondensiert,  zum Beispiel in wässeriger Lösung erwärmt  oder in schwach alkalischer Lösung in der  Kälte einige Stunden stehen     lässt,    wobei sich  der     Ringschluss    zum     Pyrazolon    vollzieht,

    ohne     dass    eine     Verseifung    der     Karbonsäure-          estergruppe    eintritt.  



  Gegenstand dieses Patentes ist ein Ver  fahren zur     Dirstellung    des     1-(4*-Sulfophe-          nyl)-5-pyrazololi-3-karl)onsäureäthylesters.       <I>Beispiel:</I>  <B>188</B> Teile     p-Sulfophenylhydrazin    worden  in<B>1000</B> Teilen Wasser suspendiert; dazu  setzt man<B>230</B> Teile des     Natriumsalzes    des       Oxalessigätllylesters    und     lässt    etwa eine  Stunde in der Kälte stehen; dann erhitzt  man das Gemisch langsam zum Sieden, nach  etwa 1-2 Stunden beginnt die Lösung un  ter     Abscheidung    von Kristallen zu stossen.

    Dann gibt man so viel Wasser hinzu,     dass     wieder in der Hitze eine klare Lösung ent  steht und hält noch<B>1-2</B> Stunden im Sie  den. Beim Erkalten kristallisiert- der     Sulfo--          pyrazolonkarbonsäureäthylester    aus; durch  Zusatz von verdünnten Säuren kann aus der  Lauge noch eine weitere Menge an Ester  erhalten werden. Das so erhaltene Produkt  kann durch     Umkristalfisieren    aus Wasser ge  reinigt werden und stellt dann ein weisses  Pulver dar.



  Process for the preparation of the 1- (9-stilfophonyl) -5-pyrazi) loii-3-carboxylic acid ethyl ester. It has been found that the esters of sulfop #, riizolonlzarboxylic acid of the following composition:

    
EMI0001.0004
    where R is an alkyl radical and X is an aromatic nucleus, its homologues and substitution products, can be prepared in such a way that the hydrazones are condensed from the corresponding X-hydrazinesulfonic acids (X as above) and oxaloacetic esters, for example heated in aqueous solution or let stand in the cold in a weakly alkaline solution for a few hours, during which the ring closure to the pyrazolone takes place

    without saponification of the carboxylic acid ester group occurring.



  The subject of this patent is a process for the preparation of the 1- (4 * -Sulfophenyl) -5-pyrazololi-3-karl) on acid ethyl ester. <I> Example: </I> <B> 188 </B> parts of p-sulfophenylhydrazine were suspended in <B> 1000 </B> parts of water; to do this, <B> 230 </B> parts of the sodium salt of the oxalacetyllyl ester are added and left to stand in the cold for about an hour; then the mixture is slowly heated to the boil, after about 1-2 hours the solution begins to collide with the separation of crystals.

    Then you add enough water that a clear solution is formed again in the heat and you keep it for <B> 1-2 </B> hours. On cooling, the ethyl sulfo pyrazolone carboxylate crystallizes out; By adding dilute acids, a further amount of ester can be obtained from the lye. The product obtained in this way can be purified by recrystallization from water and is then a white powder.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung des 1-(4'- Sulfophenyl) <B>- 5 -</B> pyrazolon <B>- 3 -</B> karbonsäure- äthylesters, dadurch gekennzeichnet, dass man ein Salz des aus p-Sulfophenylhydrazin und Oxalessigäthylester erhältlichen Hydra- zons in wässeriger Lösung erwärmt. PATENT CLAIM: Process for the preparation of the 1- (4'-sulfophenyl) <B> - 5 - </B> pyrazolon <B> - 3 - </B> carboxylic acid ethyl ester, characterized in that a salt of the p- Sulphophenylhydrazine and oxalacetic ethyl ester available hydrazones heated in aqueous solution. Ei, stellt -,etrochnet ein farbloses Pulver dar, das in n Wasser leicht löslieh ist und zür Herstellung von Farbstof fen dienen soll. Egg, represents -, etrocessed a colorless powder that is easily soluble in water and is intended to be used for the production of dyes.
CH119718D 1924-11-27 1925-11-24 Process for the preparation of the 1- (4'-sulfophenyl) -5-pyrazolone-3-carboxylic acid ethyl ester. CH119718A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE119718X 1924-11-27

Publications (1)

Publication Number Publication Date
CH119718A true CH119718A (en) 1927-04-01

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ID=5656185

Family Applications (1)

Application Number Title Priority Date Filing Date
CH119718D CH119718A (en) 1924-11-27 1925-11-24 Process for the preparation of the 1- (4'-sulfophenyl) -5-pyrazolone-3-carboxylic acid ethyl ester.

Country Status (1)

Country Link
CH (1) CH119718A (en)

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