CH204741A

CH204741A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.

Info

Publication number: CH204741A
Authority: CH
Inventors: Gesellschaft Fuer Chemis Basel
Original assignee: Chem Ind Basel
Priority date: 1935-07-23
Filing date: 1935-07-23
Publication date: 1939-05-15

Description

  

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     Imidazoldihydrids-(4,ö).       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung eines in       2-Stellung    substituierten     Imidazol-dihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     2-Athoxy-phenoxyacetimino-          äther    mit     Athylendiamin    umsetzt.  



  Das so gewonnene     2-(2'-Äthoxy-phenoxy-          methyl)-imidazol-dihydrid-(4,5)    bildet ein  farbloses Hydrochlorid vom F. 138 bis 139  .  



  Die neue Verbindung     kann    als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>       22   <B>6</B>     Teile    2 -     Äthoxy    -     phenoxyacetimino-          äthyläther-hydrochlorid    der Formel  
EMI0001.0017     
    (hergestellt aus dem beim Erhitzen von     Gu-          äthol    mit     Chloracetonitril    in     Acetonlösung       und Gegenwart von     Pottasche    entstehenden  2 -     Äthoxy    -     phenoxyacetonitril,        Kp4    125  ,  F.

   44  ), aus dem sich während der Umset  zung     2-Athoxy-phenoxyacetiminoäthyläther     bildet, werden in absolutem Alkohol gelöst.  Man fügt ziemlich rasch 6 Teile     Athylen-          diamin    hinzu, erhitzt langsam auf<B>100'</B> und  hält einige Stunden bei dieser Temperatur.  Hernach vertreibt man den Alkohol, versetzt  den Rückstand mit Natronlauge und extra  hiert erschöpfend mit Benzol. Nach dem       Trocknen    über Pottasche     und        nachherigem     Vertreiben des Benzols bleibt das     2-(2'-Athoxy-          phenoxymethyl)-imidazoldihydrid-(4,5)    der  Formel  
EMI0001.0034     
    zurück.

    An Stelle von 2 -     Äthoxy-        phenoxyacet-          iminoäthyläther    kann ebensogut ein anderer           -lther,    wie z. B. der     Methyl-,        Propyl-    oder       Butyläther    Verwendung finden.  



  Statt vom salzsauren Salz des     2-Ällioxy-          plienoxyacetiminoä.thers    kann man auch von  einem andern Salze, wie z. B. vom     bromwas-          serstoffsauren,    vom     schwefelsauren    oder vom       inethylscliwefelsauren    Salz ausgehen.



  Process for the preparation of an imidazole dihydride (4, ö) substituted in the 2-position. The present patent relates to a process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, which is characterized in that a 2-ethoxy-phenoxyacetimino ether is reacted with ethylenediamine.



  The 2- (2'-ethoxyphenoxymethyl) imidazole dihydride (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 138 to 139.



  The new compound can be used as a medicine.



  <I> Example: </I> 22 <B> 6 </B> parts 2 - ethoxy - phenoxyacetimino ethyl ether hydrochloride of the formula
EMI0001.0017
    (made from the 2-ethoxy-phenoxy-acetonitrile formed when guethol is heated with chloroacetonitrile in acetone solution and in the presence of potash, Kp4 125, F.

   44), from which 2-ethoxy-phenoxyacetiminoethyl ether is formed during the implementation, are dissolved in absolute alcohol. 6 parts of ethylene diamine are added fairly quickly, heated slowly to <B> 100 '</B> and held at this temperature for a few hours. The alcohol is then driven off, the residue is mixed with sodium hydroxide solution and then exhaustively with benzene. After drying over potash and subsequent driving off of the benzene, the 2- (2'-ethoxyphenoxymethyl) imidazole dihydride (4,5) of the formula remains
EMI0001.0034
    back.

    Instead of 2 - ethoxyphenoxyacet iminoäthyläther can just as well another ether, such as z. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 2-Ällioxy- plienoxyacetiminoä.thers one can also use another salt, such as z. B. from the hydrobromic acid, from the sulfuric acid or from the methylsulfuric acid salt.

Claims

PATEN TAN SPRUCH Process for the preparation of an Imida.zoldihy diids substituted in the 2-position - (, 4,5), characterized in that a 2-Ätlioxy-phenoxya.cetiminoäther is reacted with Äthylen- diaiiiin. The 2- (2 'ethoxy-phenoxy-methyl) -imida.zol-dihydride- (4,5) obtained in this way

forms a colorless hydrochloride from F. <B> 1.38 </B> to <B> 1.39 </B> ". The new compound can be used as a medicament. UN TERAN SPM CHE 1. Process according to patent claim, characterized in that .ss to implement 2-ethoxy-phenoxyacetiminoäthyläther ver used.

- ?. Method according to patent claim, characterized in that a? - Xtlioxy - phenoxy aeetiminoäther ver -endet, which was obtained from a salt thereof. 2.

Process according to patent claim and sub-claim 2, characterized in that a 2-ethoxy-plienoxyaoetimiiloätlier is used for the reaction, which wants to obtain the same from a .1-hydrohalide thereof. 4. Procedure according to. Claim and the subclaims? and 3, characterized in that a? -ethoxy-phenoxyacetiminoether is used for the reaction, which was obtained from the hydrochloride of the same.

Method according to patent claim and subclaims 1 to 4, characterized in that one can implement? Ethoxy-phenoxyacetiminoäthyläther used ver. which was obtained from the hydrochloride of the same ben.