CH204727A

CH204727A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.

Info

Publication number: CH204727A
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-(4,5).       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     4-Methoxyphenylacetimino-          äther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(4'-Methoxybenzyl)-          imidazol-dihydrid-(4,5)    bildet farblose Kri  stalle vom F. 118 bis 120'. Sein     Hydrochlo-          rid    ist ein farbloses Kristallpulver.  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>       4-Methoxyphenylacetiminoäthyläther-hy-          drochlorid    der Formel  
EMI0001.0015     
    (hergestellt aus 1,4 Teilen     4-Methoxyphenyl-          a.cetonitril),    aus dem sich während der Um  setzung 4 - Methoxyphenylacetiminoäthyl-         äther    bildet, wird in 12 Teilen absolutem  Alkohol gelöst. Man fügt ziemlich rasch  1 Teil     Äthylendiamin    hinzu, erhitzt langsam  auf<B>100'</B> und hält einige     Stunden    bei dieser  Temperatur.

   Hernach vertreibt man den Al  kohol, versetzt den Rückstand bei guter Eis  kühlung mit Natronlauge, wobei das     2-(4'-          Methoxy-benzyl)-imidazoldihydrid-(4,5)    der  Formel  
EMI0001.0023     
    auskristallisiert. Es wird nach dem Trock  nen aus     Toluol    umkristallisiert.  



  An Stelle von     4-Methoxyphenylacetimino-          äthyläther    kann ebensogut ein anderer Äther,  wie z. B. der     Methyl-,        Propyl-    oder     Butyl-          äther    Verwendung finden.  



  Statt vom salzsauren Salz des     4-Methoxy-          phenylacetiminoäthers        kann    man auch von  einem andern Salze, wie z. B. vom bromwas-           serstoffsauren,    vom     schwefelsauren    oder vom       methylschwefelsauren    Salz ausgehen.



  Process for the preparation of an imidazole dihydride (4,5) 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 4-methoxyphenylacetimino ether is reacted with ethylenediamine.



  The 2- (4'-methoxybenzyl) - imidazole-dihydride- (4,5) obtained in this way forms colorless crystals with a melting point of 118 to 120 '. Its hydrochloride is a colorless crystal powder.



  The new compound can be used as a medicine.



  <I> Example: </I> 4-methoxyphenylacetiminoethyl ether hydrochloride of the formula
EMI0001.0015
    (made from 1.4 parts of 4-methoxyphenyl a.cetonitrile), from which 4 - methoxyphenylacetiminoethyl ether is formed during the reaction, is dissolved in 12 parts of absolute alcohol. 1 part ethylenediamine is added fairly quickly, heated slowly to <B> 100 '</B> and held at this temperature for a few hours.

   The alcohol is then sold, the residue is treated with sodium hydroxide solution while cooling well with ice, the 2- (4'-methoxy-benzyl) -imidazole dihydride (4.5) of the formula
EMI0001.0023
    crystallized out. After drying it is recrystallized from toluene.



  Instead of 4-Methoxyphenylacetimino- äthyläther, another ether, such as z. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 4-Methoxyphenylacetiminoäthers you can also use another salt, such as. B. start with the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims

PATENTAN SPRUCI3 Process for the preparation of an imidazoldihydrids- (4,5) substituted in the 2 position, characterized in that a 4-methoxyphenylacetiminoether is reacted with lithylenediamine. The? - (4'-3 # letboxybenzy 1) - imida.zol-dihydrid- (4,5) obtained in this way forms colorless crystals of the r. <B> 118 </B> to 120 '. Its hydrochloride is a colorless crystal powder.

The new compound can be used as a medicine. SUB-CLAIM 1. Process according to claim, characterized in that 4-i4-thoxyphenylacetiminoethyl ether is used for the reaction. 2. The method according to claim, characterized in that a 4-blethox5-phenylacetiminoether is used for unisposition. Which was obtained from a salt thereof. 3.

Process according to patent claim and sub-claim 2, characterized in that a 4-IVle- tliox3r-plienvlaeetiiuinoether is used for the reaction "which was obtained from a hydrohalide of the same. 4. Process according to patent claim and dependent claims 3 and 3, characterized that a 4-lletlioxyplienvlacetiminoether obtained from the hydrochloride of the same is used for the reaction.

Process according to patent claim and the dependent claims 1 to 4, characterized in that for the reaction 4-31e- l, liox -,> plienylacetiminaätliy läther used which was obtained from the hydrochloride thereof.