CH204734A

CH204734A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.

Info

Publication number: CH204734A
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        sabstitaierten        Imidazoldii)ydrids-(4,ö).       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung eines in       2-Stellung        substitutierten        Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     2-Methoxy-phenoxyacetimino-          äther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(2'-Methoxy-phen-          oxymethyl)-imidazoldihydrid-(4,5)    bildet ein  farbloses     Hydrochlorid    vom F. 167 bis<B>169'.</B>  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  3,5 Teile     2-Methoxy-phenoxyacetimino-          äthyläther-hydrochlorid    der Formel  
EMI0001.0016     
    (hergestellt aus dem beim Erhitzen von     Gua-          jacol    mit     Chloracetonitril    in     Acetonlösung     und Gegenwart von Pottasche entstehenden         2-Methoxy-phenoxyacetonitril,        gp."   <B>110</B> bis  112  ), aus dem sich während der Umsetzung       2-Methoxy-phenoxyacetiminoäthyläther    bil  det, werden in 6 Teilen     absolutem    Alkohol  gelöst.

   Man fügt ziemlich rasch 1 Teil     Äthy-          lendiamin    hinzu, erhitzt langsam auf 100    und hält einige Stunden bei dieser Tempera  tur.     Hernach    vertreibt man den Alkohol,  versetzt den Rückstand mit Natronlauge und  extrahiert erschöpfend mit Benzol. Nach dem       Trocknen    über Pottasche und     nachherigem     Vertreiben des Benzols bleibt das     2-(2'-Me-          thoxy    -     phenoxy    -     methyl)    -     imidazoldihydrid-          (4,5)    der Formel  
EMI0001.0036     
    zurück.

    An Stelle von     2-Methoxy-phenoxyacet-          iminoäthyläther    kann ebensogut ein anderer      Äther, wie z. B. der     --L#lethyl-,        Propyl-    oder       Butyläther    Verwendung finden.  



  Statt vom salzsauren Salz des     2-Dlethoxy-          phenoxyacetiminoäthers    kann man auch von  einem andern Salze, wie z. B. vom     brom-          wasserstoffsauren,    vom schwefelsauren oder  vom     methylschwefelsauren    Salz ausgehen.



  Process for the preparation of an imidazolii) ydrids- (4, ö) sabstaged 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-methoxyphenoxyacetimino ether is reacted with ethylenediamine.



  The 2- (2'-methoxy-phenoxymethyl) -imidazole dihydride- (4,5) obtained in this way forms a colorless hydrochloride from F. 167 to <B> 169 '. </B>



  The new compound can be used as a medicine.



  <I> Example: </I> 3.5 parts of 2-methoxyphenoxyacetimino ethyl ether hydrochloride of the formula
EMI0001.0016
    (manufactured from the 2-methoxyphenoxyacetonitrile formed when guacacol is heated with chloroacetonitrile in acetone solution and the presence of potash, gp. "<B> 110 </B> to 112), from which 2-methoxy- phenoxyacetiminoäthyläther bil det are dissolved in 6 parts of absolute alcohol.

   One part of ethylenediamine is added fairly quickly, heated slowly to 100 and held at this temperature for a few hours. The alcohol is then driven off, the residue is mixed with sodium hydroxide solution and extracted exhaustively with benzene. After drying over potash and then driving off the benzene, the 2- (2'-methoxy-phenoxy-methyl) -imidazole dihydride (4,5) of the formula remains
EMI0001.0036
    back.

    Instead of 2-methoxy-phenoxyacet- iminoäthyläther, another ether, such as z. B. the --L # ethyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 2-Dlethoxyphenoxyacetiminoäthers you can also use another salt, such as. B. start from the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims

PATENT CLAIM: Process for the preparation of an imidazoldiliy substituted in the 2-position drids- (4,5), characterized in that a 2-3lethoxy-phenoxyacetiniinoether is reacted with ethylenediamine. The 2- (2'-methoxyphenoxymethyl) imidazole dihydride (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 167 to 169. The new compound can be used as a medicine. SUBCLAIMS 1.

Process according to patent claim, characterized in that 2-methoxyphenoxyacetiminoethyl ether is used for the reaction. \ ?. Process according to patent claim, characterized in that a 2-3lethoxy-phenoxyacetiminoether is used for the reaction, which was obtained from a salt thereof. 3.

Process according to patent claim and un teran claim 2, characterized in that a 2-methoxyphenoxy acetimino ether is used for the reaction, which was obtained from a hydrohalide thereof. 4. The method according to claim and the dependent claims 2 and 3, characterized in that a 2-111ethoxy - phenoxyacetiminoether is used for the reaction, which was obtained from the hydrochloride of the same. 5.

Process according to patent claim and the dependent claims 1 to 4, characterized in that 2 - L% fethoxyphenoxyacetiminoä.thyläther is used for the reaction, which was obtained from the hydrochloride of the same.