CH242275A - Process for the preparation of a new benzenesulfonamide derivative. - Google Patents

Process for the preparation of a new benzenesulfonamide derivative.

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Publication number
CH242275A
CH242275A CH242275DA CH242275A CH 242275 A CH242275 A CH 242275A CH 242275D A CH242275D A CH 242275DA CH 242275 A CH242275 A CH 242275A
Authority
CH
Switzerland
Prior art keywords
preparation
amino
benzenesulfonamide derivative
new
derivative
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH242275A publication Critical patent/CH242275A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung eines neuen     Benzolsulfonamidderivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines     neuen          Benzolsulfonamidderivates,    das dadurch ge  kennzeichnet ist, dass man     p-Aminö-benzol-          sulfonylguanidin    auf ein funktionelles Derivat  des     Acetylacetons,    das unter Bildung des       Pyrimidinringes    reagiert,     wie        zum.    Beispiel  ein     Imid,        Acetol    oder     Mercaptol,        einwirken     lässt.  



  Das so erhaltene     2-(p-Amino-benzolsul-          fonamido)-4,6-dimethyl-pyrimidin    schmilzt       aus    Alkohol umkristallisiert bei 193-196 .  Es soll als Arzneimittel sowie als Zwischen  produkt     Verwendung    finden.  



  Die Umsetzung lässt sich in An- oder Ab  wesenheit von Lösungsmitteln zum Beispiel       durch,    blosses     Erhitzen    der Komponenten  durchführen. Es kann auch     in.    Gegenwart  von     Kondensationsmitteln    gearbeitet werden.

    <I>Beispiel:</I>  214 g     p-Amino-benzolsidf        onylguanidin,     erhalten durch Umsetzung von p-Acetyl-         amino-benzolsulfochlorid    mit     Guanidinnitrat     in Aceton unter Zusatz von Natronlauge und  nachträgliche     Verseifung    mit Salzsäure, wer  den mit 99 g     Acetylacetonimid    4 Stunden im  Ölbad von 1,90  am     Rückfluss    erhitzt.

   Der  erkaltete Rückstand wird in verdünnter     Salz-          säure    gelöst und die salzsaure Lösung     in          einen        überschuB    von verdünnter Natronlauge  unter Rühren eingegossen. Die alkalische  Lösung lässt man 6 Stunden stehen, filtriert  von etwas     unumgesetztem        p-Amino-benzol-          sulfonylguanidin    ab und fällt aus dem Fil  trat durch Neutralisieren mit Salzsäure das       gebildete        2-(p-Amino-benzolsulfonamido)-4,6-          dimethyl-pyrimidin    aus.

   Man kann es durch       Umkristallisieren    aus Alkohol reinigen;  F. 193-196 .



  Process for the preparation of a new benzenesulfonamide derivative. The present patent is a process for the preparation of a new benzenesulfonamide derivative, which is characterized in that p-Amino-benzenesulfonylguanidine is based on a functional derivative of acetylacetone, which reacts to form the pyrimidine ring, such as. For example, an imide, acetol or mercaptol, can act.



  The 2- (p-amino-benzenesulfonamido) -4,6-dimethyl-pyrimidine thus obtained melts from alcohol, recrystallized at 193-196. It should be used as a medicinal product and as an intermediate product.



  The reaction can be carried out in the presence or absence of solvents, for example, by simply heating the components. It is also possible to work in the presence of condensing agents.

    <I> Example: </I> 214 g of p-Amino-benzenesidefonylguanidine, obtained by reacting p-acetyl-amino-benzenesulfochloride with guanidine nitrate in acetone with the addition of sodium hydroxide solution and subsequent saponification with hydrochloric acid, who with 99 g of acetylacetonimide 4 Heated to reflux in a 1.90 oil bath for hours.

   The cooled residue is dissolved in dilute hydrochloric acid and the hydrochloric acid solution is poured into an excess of dilute sodium hydroxide solution with stirring. The alkaline solution is left to stand for 6 hours, some unreacted p-aminobenzenesulfonylguanidine is filtered off and the 2- (p-aminobenzenesulfonamido) -4,6-dimethylpyrimidine formed is precipitated from the filtrate by neutralization with hydrochloric acid out.

   It can be purified by recrystallizing it from alcohol; F. 193-196.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen Benzolsalfonamidderivates, dadurch gekenn zeichnet, dass man p-Amino-benzolsulfonyl- guanidin auf ein funktionelles Derivat des Acetylacetons, das unter Bildung des Pyr- imidinringes reagiert, einwirken lässt. Das so erhaltene 2-(p-Amino-benzolsul- fonamido)-4, PATENT CLAIM: Process for the production of a new benzenesalfonamide derivative, characterized in that p-amino-benzenesulfonylguanidine is allowed to act on a functional derivative of acetylacetone, which reacts to form the pyrimidine ring. The thus obtained 2- (p-amino-benzenesulfonamido) -4, 6-dimethyl-pyrimidin schmilzt aus Alkohol umkristallisiert bei 193-3.96 . Es soll als Arzneimittel sowie als Zävischen- produkt Verwendung finden. 6-dimethyl-pyrimidine melts recrystallized from alcohol at 193-3.96. It should be used as a medicinal product and as a cervical product.
CH242275D 1941-05-23 1942-05-22 Process for the preparation of a new benzenesulfonamide derivative. CH242275A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE242275X 1941-05-23
CH235565T 1942-05-22

Publications (1)

Publication Number Publication Date
CH242275A true CH242275A (en) 1946-04-30

Family

ID=25728003

Family Applications (1)

Application Number Title Priority Date Filing Date
CH242275D CH242275A (en) 1941-05-23 1942-05-22 Process for the preparation of a new benzenesulfonamide derivative.

Country Status (1)

Country Link
CH (1) CH242275A (en)

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