CH204726A

CH204726A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.

Info

Publication number: CH204726A
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-(4,6).            Gegenstand    des vorliegenden Patentes     ist     ein Verfahren zur Darstellung eines     in    2  Stellung     substituierten        Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     Phenylacetiminoäther    mit       Äthylendiamin    umsetzt.  



  Das so ,gewonnene     2-Benzyl-imidazol-,di.          hydrid-(4,5)    bildet farblose     Kristalle    vom  F. 61 bis 62       und    vom KP" 147'. Sein  Hydrochlorid ist ein farbloses     Kristallpulver     vom F.<B>168</B> bis<B>170'.</B>  



  Die neue     Verbindung    kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  Das salzsaure 'Salz ,des     Phenyl-acetimino-          ä.thyläthers    der     Formel          CEHr'CH2@        0C        -HCl     (hergestellt aus 1-2 Teilen     Benzylcyanid)     wird mit     .8    Teilen     Äthylendiaminhydrat,    das       durch    wenig Alkohol     verdünnt    ist, versetzt,    wobei die     Kristalle    in Lösung gehen.

   Man       erwärmt        dann.    auf dem     Wasserbad,        bis    der       Ammoniakgeruch        verschwunden        ist,    kühlt  ab, gibt     konzentrierte    Kalilauge hinzu und  nimmt .das     ausgeschiedene    '01     in    Äther auf:

    Die Lösung wird mit     Kaliumcarbonat        und          -hydrogyd    getrocknet; nach -dem Eindampfen  bleibt ein helles 01 zurück,     das        unter        @    mm  Druck bei 147       überdestilliert    und     in    der  Vorlage zu einer weissen     Kristallmasse    er  starrt. Das 2 -     Benzylimidazoldihydrid    - (4,5)  der Formel  
EMI0001.0049     
    erhält man     in        einer        Ausbeute    von<B>90%</B> der  Theorie.

   Das     Hydrochlorid    hat den F.168  bis 170  .  



  An Stelle von     Phenylacetiminoäthysäther     kann ebensogut ein anderer Äther, wie z. B.  der     Methyl-,        Propyl-    oder     Butyläther,    Ver  wendung     finden.              Statt    vom salzsauren Salz des     Phenyl-          acetiminoäthers    kann man     auch    von einem  andern Salze, wie z. B. vom     bromwasserstoff-          sauren,    vom     schwefelsauren    oder vom     methyl-          sch@vefelsauren    Salz ausgehen.



  Process for the preparation of a 2-substituted imidazole dihydride (4,6). The present patent relates to a process for the preparation of an imidazole dihydride (4,5) which is substituted in the 2 position and which is characterized in that a phenylacetimino ether is reacted with ethylenediamine.



  The 2-benzyl-imidazole-, di. hydride- (4,5) forms colorless crystals from F. 61 to 62 and from KP "147 '. Its hydrochloride is a colorless crystal powder from F. <B> 168 </B> to <B> 170'. </ B >



  The new compound can be used as a medicine.



  <I> Example: </I> The hydrochloric acid salt of phenyl-acetimino-ethyl ether of the formula CEHr'CH2 @ 0C -HCl (made from 1-2 parts of benzyl cyanide) is mixed with .8 parts of ethylenediamine hydrate, which by little Alcohol is diluted, added, whereby the crystals go into solution.

   One then warms up. on the water bath until the ammonia smell has disappeared, cools down, adds concentrated potassium hydroxide and absorbs the '01 which has been separated out in ether:

    The solution is dried with potassium carbonate and potassium hydrogen; After evaporation, a light oil remains, which distills over under @ mm pressure at 147 and in the template it stares to form a white crystal mass. The 2 - benzylimidazole dihydride - (4,5) of the formula
EMI0001.0049
    is obtained in a yield of <B> 90% </B> of theory.

   The hydrochloride has the F.168 to 170.



  Instead of Phenylacetiminoäthysäther another ether, such as z. B. the methyl, propyl or butyl ether, Ver use. Instead of the hydrochloric acid salt of the phenyl acetiminoether one can also use another salt, such as B. from the hydrobromic acid, the sulfuric acid or the methyl-sch @ vefelsauren salt.

Claims

PATENT CLAIM: Method for the representation of an in? Position substituted imidazole dihydride (4,5), characterized in that one sets a Pheny lacetiminoether with Xthy lenediamine. The 2 - benzyl - imidazole dihydride (4,5) obtained in this way forms colorless crystals from F. 61 to 62 and from KP. 147. Its hydrochloride is a colorless crystal powder with a temperature of 168 to 170. The new compound can be used as a medicine.

SUBClaims: 1. Method according to claim, characterized. that phenylacetiminoethyl ether is used for the reaction. 2. The method according to claim, characterized in that a phenylacetimino ether is used for the reaction, which was obtained from a salt thereof. 3. The method according to claim and sub-claim?, Characterized in that a phenylacetamine is used for the reaction, which was obtained from a hydrohalide of the same. 4th

A method according to claim and the dependent claims 2 and 3, characterized in that a phenylacetimino ether is used for the reaction, which was obtained from the hydrochloride of the same. 5. The method according to claim and the dependent claims 1 to 4, characterized in that phenylacetiminoethyl ether is used for the reaction, which was obtained from the hydrochloride of the same.