CH235436A - Process for the preparation of a reactive ester of an oxyalkylamidine. - Google Patents

Process for the preparation of a reactive ester of an oxyalkylamidine.

Info

Publication number
CH235436A
CH235436A CH235436DA CH235436A CH 235436 A CH235436 A CH 235436A CH 235436D A CH235436D A CH 235436DA CH 235436 A CH235436 A CH 235436A
Authority
CH
Switzerland
Prior art keywords
ether
preparation
reactive ester
hydrochloride
chlorobutyroimido
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 CH235436A publication Critical patent/CH235436A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms

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

Description

  

  Verfahren zur Darstellung eines reaktionsfähigen Esters eines     Ogyalkylamidins.       Es wurde gefunden, dass, man zu einem       reaktionsfähigen        Ester    eines     Ogyalkylamidins     gelangen     kann,    wenn man     einen,        y-Chlor-          butyroimidoäther    mit     Äthylendiamin    um  setzt. Zweckmässig arbeitet man in Gegen  wart eines     Lösungsmittels.     



  Das so gewonnene 2 - [y -     Chlorpropyl]        -          imida.zolin    der Formel  
EMI0001.0014     
    bildet ein farbloses     Hydrochlorid    vom F. l45 .  In Wasser ist es leicht löslich. Es soll als       Zwischenprodukt    Verwendung finden.  



  <I>Beispiel:</I>  185 Teile     y-Chlorbutyroimid.oäthyläther-          hydrochlorid    (hergestellt durch Einwirkung       von    Chlorwasserstoff auf ein Gemisch äqui  valenter Mengen     y-Chlorbutyronitril    und  Äthylalkohol), aus dem sich während der  Reaktion die freie Base bildet, werden unter       gutem        Rühren;    zu     einer    eisgekühlten     Lösung     von 60 Teilen     Äthylendiamin    in 400 Teilen         absolutem    Alkohol gegeben.

   Nach etwa einer  Stunde setzt man eine Lösung von 86 Teilen       Chlorwasserstoffsäure    in 500,     Teilen        äbsolu-          tem    Alkohol zu und erwärmt ,das     ReakHons-          gemiech    langsam auf     Zimmertemperatur.    Das  entstandene     Ammonchlorid    wird     abgenutscht,     das klare Filtrat eingedampft und der Rück  stand aus einem     Äther-Alkohol        Gemisch        um-          kristallisiert,

          wobei    das     2-[y-Chlorpropyl]-          imidazolin-.hydrochlori@d    in     .farblosen    Kri  stallen ausfällt.  



  Statt :des     y-Chlorbutyroimidoäthyläthers     kann auch ein anderer Äther, wie z. B.     der          Methyl-,        Propyl-,        Butyl-    oder     Phenyläther,     Verwendung finden.  



  An     Stelle    des salzsauren Salzes des       y-Chlorbutyroimidoäthyläthers,    kann auch die  freie Base selbst, oder ein anderes .Salz,     wie     z. B. das     Hydrobromi.d    oder     schwefelsaure     Salz, als     Ausgangsmaterial        benützt    werden.



  Process for the preparation of a reactive ester of an ogyalkylamidine. It has been found that a reactive ester of an ogyalkylamidine can be obtained if a, γ-chlorobutyroimido ether is implemented with ethylenediamine. It is expedient to work in the presence of a solvent.



  The 2 - [y - chloropropyl] - imida.zoline of the formula obtained in this way
EMI0001.0014
    forms a colorless hydrochloride of F. 145. It is easily soluble in water. It should be used as an intermediate product.



  <I> Example: </I> 185 parts of y-chlorobutyroimide.oäthyläther- hydrochloride (produced by the action of hydrogen chloride on a mixture of equivalent amounts of y-chlorobutyronitrile and ethyl alcohol), from which the free base is formed during the reaction, are under good stirring; added to an ice-cold solution of 60 parts of ethylenediamine in 400 parts of absolute alcohol.

   After about an hour, a solution of 86 parts of hydrochloric acid in 500 parts of absolute alcohol is added and the mixture is warmed, and the reaction mixture slowly to room temperature. The ammonium chloride formed is filtered off with suction, the clear filtrate is evaporated and the residue is recrystallized from an ether-alcohol mixture,

          where the 2- [y-chloropropyl] - imidazolin-.hydrochlori@d precipitates in .colorless crystals.



  Instead of: the y-chlorobutyroimidoethyl ether, another ether, such as z. B. the methyl, propyl, butyl or phenyl ethers, use.



  Instead of the hydrochloric acid salt of y-chlorobutyroimidoethyl ether, the free base itself, or another .Salz, such as. B. the Hydrobromi.d or sulfuric acid salt, can be used as starting material.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines reak tionsfähigen Esters eines Ogyalkylamidins, dadurch gekennzeichnet, duss man einen y-C'hlorbutyroimidoäther mit Äthylendiamin umsetzt. Das so gewonnene 2 - [y - Chlorpropyll - imidazolin der Formel EMI0002.0009 bildet ein farbloses Hydrochlorid vom F. 145 . In Warsser ist es leicht löslich. PATENT CLAIM: Process for the preparation of a reactive ester of an ogyalkylamidine, characterized in that a γ-chlorobutyroimido ether is reacted with ethylenediamine. The 2 - [y - chloropropyll - imidazoline of the formula obtained in this way EMI0002.0009 forms a colorless hydrochloride of F. 145. It is easily soluble in Warsser. Es soll als Zwischenprodukt Verwendung finden. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man zur Um setzung y-Chlorbutyroimidoäthyläther ver wendet. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man einen y-Chlor- butyroimidoäther verwendet, der aus einem Salz desselben erhalten wurde. 3. It should be used as an intermediate product. SUBClaims: 1. The method according to claim, characterized in that y-chlorobutyroimidoethyl ether is used to implement. 2. The method according to claim, characterized in that a γ-chloro-butyroimidoether is used, which was obtained from a salt thereof. 3. Verfahren nach Patentanspruch und Unteranspruch 2, dadurch gekennzeichnet, dass man einen y-Chlorbutyroimidoäther ver wendet, . der aus einem Hydrohalogenid desselben erhalten wurde. 4. Verfahren nach Patentanspruch und den Unteransprüchen 2, und 3, dadurch ge kennzeichnet, dass man einen y-Chlorbutyro- imidoäther verwendet, der aus einem Hydro- chlorid desselben. erhalten wurde. 5. Process according to claim and dependent claim 2, characterized in that a γ-chlorobutyroimido ether is used. obtained from a hydrohalide thereof. 4. The method according to claim and the dependent claims 2 and 3, characterized in that a γ-chlorobutyroimidoether is used, which is the same from a hydrochloride. was obtained. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man in Gegen wart eines Lösungsmittels arbeitet. U. Verfahren nach Patentanspruch und .den. Unteransprüchen 1 bis 4, dadurch ge kennzeichnet, dass man y-Chlorbutyroimido- äthyläther verwendet, der aus dem Hydro- chlorid desselben erhalten wurde. Process according to claim, characterized in that one works in the presence of a solvent. U. method according to patent claim and .den. Dependent claims 1 to 4, characterized in that γ-chlorobutyroimido ethyl ether is used, which was obtained from the hydrochloride of the same.
CH235436D 1938-05-11 1938-05-11 Process for the preparation of a reactive ester of an oxyalkylamidine. CH235436A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH229606T 1938-05-11
CH235436T 1938-05-11

Publications (1)

Publication Number Publication Date
CH235436A true CH235436A (en) 1944-11-30

Family

ID=25727371

Family Applications (1)

Application Number Title Priority Date Filing Date
CH235436D CH235436A (en) 1938-05-11 1938-05-11 Process for the preparation of a reactive ester of an oxyalkylamidine.

Country Status (1)

Country Link
CH (1) CH235436A (en)

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