CH280182A - Process for the production of a new guanidine derivative. - Google Patents

Process for the production of a new guanidine derivative.

Info

Publication number
CH280182A
CH280182A CH280182DA CH280182A CH 280182 A CH280182 A CH 280182A CH 280182D A CH280182D A CH 280182DA CH 280182 A CH280182 A CH 280182A
Authority
CH
Switzerland
Prior art keywords
production
oxy
guanidine derivative
new
new guanidine
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag 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 Cilag Ag filed Critical Cilag Ag
Publication of CH280182A publication Critical patent/CH280182A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines

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

Description

  

  Verfahren zur Herstellung eines neuen     Guanidinderivates.            Genenstand    des Patentes ist ein Verfahren  zur Herstellung eines neuen     Guanidinderiva-          tes,    nämlich des     4-Carboniethoxy--3-oxy-phenyl-          guanidins.    Die Verbindung soll als Zwischen  produkt zur Herstellung von Arzneimitteln  verwendet werden. Das den Gegenstand des  vorliegenden Patentes bildende Verfahren ist       dadurch    gekennzeichnet, dass man     4-Amino-          2-oxy-benzoesätiremethylester    mit     Cy        anamid     kondensiert.

   Die Kondensation kann in einem       Lösungsmittel,    z. B. in     Äthanol,    durchgeführt  werden. Es ist aber auch möglich, die Umset  zung durch Schmelzen der beiden Reaktions  partner herbeizuführen. Zweckmässig arbeitet  man in     Gegenwart    saurer Kondensationsmit  tel, z. B. in     (egenwart    von Mineralsäuren. Das  so erhaltene     4-Cai-bomethoxy-3-oxy-phenyl-          guanidin    bildet farblose, bei 195 bis<B>1960</B>  schmelzende Blättchen, die sieh leicht in ver  dünnten Mineralsäuren     -Lind        Alkalilaugen     lösen. Die Verbindung kann im     Hoehvaktnim     sublimiert werden.

   Die freie Säure schmilzt  bei 296".  



  <I>Beispiel:</I>  Eine     Mischung    von 300 g     4-Amino-2-oxy-          benzoesäuremethylester    und 300 g     Cy        anamid     werden auf dem Dampfbad bis zur Bildung  einer homogenen Schmelze erhitzt. Unter Rüh  ren lässt man langsam 800     em3        ä.thanolische          Chlorwasserstofflösting    einfliessen. Nach dem  Abklingen der heftigen Reaktion erhitzt man  noch eine Stunde am     Rüekflusskühler    und    lässt dann einige Zeit stehen.

   Anschliessend  verdampft man das Ganze zur Trockne und       seliüttelt    den Rückstand mit     Natriumbicarbo-          natlösung.    Das Unlösliche wird abgesaugt, ge  trocknet und aus Chlorbenzol umkristallisiert.  Man erhält so das     4-Carbomethoxy--3-oxy-phe-          nyl-gtianidin    in farblosen Blättchen, die bei  195 bis 196  schmelzen. Die Verbindung kann  auch durch     Hochvakuumsublimation    gereinigt.  werden. Sie löst sich leicht in verdünnten Mi  neralsäuren und     Alkalilaugen.    Die durch Hy  drolyse mit     Natriumcarbonatlösung    erhältliche  freie Säure schmilzt bei 296 .



  Process for the production of a new guanidine derivative. The subject matter of the patent is a process for the production of a new guanidine derivative, namely 4-carboniethoxy-3-oxy-phenyl-guanidine. The compound is intended to be used as an intermediate in the manufacture of drugs. The method forming the subject of the present patent is characterized in that 4-amino-2-oxy-benzoesätiremethylester is condensed with cyanamide.

   The condensation can be carried out in a solvent, e.g. B. in ethanol. But it is also possible to bring about the implementation by melting the two reactants. It is expedient to work in the presence of acidic condensation agents, e.g. B. in (present of mineral acids. The 4-Cai-bomethoxy-3-oxy-phenyl-guanidine thus obtained forms colorless, melting between 195 and 1960, which look easily in dilute mineral acids -ind Dissolve alkali solutions The compound can be sublimed in the Hoehvaktnim.

   The free acid melts at 296 ".



  <I> Example: </I> A mixture of 300 g of 4-amino-2-oxybenzoic acid methyl ester and 300 g of cyanamide are heated on the steam bath until a homogeneous melt is formed. While stirring, slowly pour in 800 em3 of an ethanolic hydrogen chloride solution. After the vigorous reaction has subsided, the mixture is heated on the reflux condenser for another hour and then left to stand for some time.

   The whole is then evaporated to dryness and the residue is shaken with sodium bicarbonate solution. The insolubles are filtered off with suction, dried and recrystallized from chlorobenzene. In this way 4-carbomethoxy-3-oxy-phenyl-gtianidine is obtained in colorless flakes which melt at 195 to 196. The compound can also be purified by high vacuum sublimation. will. It dissolves easily in dilute mineral acids and alkaline solutions. The free acid obtained by hydrolysis with sodium carbonate solution melts at 296.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen Guanidinderivates, dadurch gekennzeichnet, dass man 4-Amino-2-oxy-benzoesäuremethyl- ester mit Cy anamid kondensiert. Das so er haltene neue d-Carbomethoxy -3-oxy-phenyl- gtianidin bildet farblose, bei 195 bis 196 schmelzende Blättchen, die sich leicht in ver dünnten Mineralsäuren und Alkalilaugen lösen. Die Verbindung kann im Hochvakuum sublimiert werden. Die freie Säure schmilzt bei 296 . PATENT CLAIM Process for the production of a new guanidine derivative, characterized in that 4-amino-2-oxy-benzoic acid methyl ester is condensed with cyanamide. The new d-carbomethoxy -3-oxy-phenyl-gtianidine obtained in this way forms colorless flakes which melt at 195 to 196 and which dissolve easily in dilute mineral acids and alkaline solutions. The compound can be sublimed in a high vacuum. The free acid melts at 296. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Kondensation in Gegenwart eines sauren Kondensationsmittels vornimmt. SUBCLAIM: Process according to claim, characterized in that the condensation is carried out in the presence of an acidic condensing agent.
CH280182D 1950-01-13 1950-01-13 Process for the production of a new guanidine derivative. CH280182A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH280182T 1950-01-13

Publications (1)

Publication Number Publication Date
CH280182A true CH280182A (en) 1952-01-15

Family

ID=4482578

Family Applications (1)

Application Number Title Priority Date Filing Date
CH280182D CH280182A (en) 1950-01-13 1950-01-13 Process for the production of a new guanidine derivative.

Country Status (1)

Country Link
CH (1) CH280182A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7956219B2 (en) * 2002-05-09 2011-06-07 Baker IDI Heart and Diabetes Amino acid analogues

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7956219B2 (en) * 2002-05-09 2011-06-07 Baker IDI Heart and Diabetes Amino acid analogues

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