CH204739A

CH204739A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.

Info

Publication number: CH204739A
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        substtuierten        Imidazol-dihydrids-          (4,5),    welches dadurch     gekennzeichnet    ist,  dass man einen     4-i#lethoxy-naphthyl-(1)-acet-          iminoäther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-[4'-Methoxy-naph-          thyl-(1')-methyl]-imidazol-dihydrid-(4,5)    bil  det farblose Kristalle vom F. 123 bis 124'.  Sein Hydrochlorid ist ein farbloses Kristall  pulver vom F. 213 bis 214  .  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  2,9 Teile     4-Methoxy-naphthyl-(1)-acet-          iminoäthylätherhydrochlorid    der Formel  
EMI0001.0015     
    (hergestellt aus 4-Methogy-naphthyl-(1)-         acetonitril),    aus dem sich während der Um  setzung     4-Methoxy-naphthyl-(1)-acetimino-          äthyläther    bildet, werden in 15 Teilen ab  solutem 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 Alkohol, versetzt den Rückstand       mit        verdünnter        Natronlauge    und     extrahiert     erschöpfend mit Benzol. Nach dem Trock  nen über Pottasche wird das 2-     [4'-Methoxy-          naphthyl    - (I') -     methyl]    -     imidazol    -     dihydrid-          (4,5)    der Formel  
EMI0001.0030     
    aus     Toluol    umkristallisiert.  



  An Stelle von     4-Methoxy-naphthyl-(1)-          acetiminoäthyläther    kann ebensogut ein an  derer Äther, wie z. B. der     Methyl-,        Propyl-          oder        Butyläther        Verwendung        finden.         Statt vom salzsauren Salz des     4-Methoxy-          naphthyl-(1)-acetiminoäthers    kann man auch  von einem andern Salze, wie z. B. vom     brom-          wasserstoffsauren,    vom schwefelsauren oder  vom     inethylschw        efelsauren    Salz ausgehen.



  Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. The subject of the present patent is a process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, which is characterized in that a 4-i # lethoxy-naphthyl- (1) -acetiminoether is mixed with ethylenediamine implements.



  The 2- [4'-methoxy-naphthyl- (1 ') -methyl] -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals with a melting point of 123 to 124'. Its hydrochloride is a colorless crystal powder from F. 213 to 214.



  The new compound can be used as a medicine.



  <I> Example: </I> 2.9 parts of 4-methoxy-naphthyl- (1) -acet- iminoethyl ether hydrochloride of the formula
EMI0001.0015
    (made from 4-methogy-naphthyl- (1) - acetonitrile), from which 4-methoxy-naphthyl- (1) -acetimino- ethyl ether is formed during the implementation, are dissolved in 15 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 driven off, the residue is mixed with dilute sodium hydroxide solution and extracted exhaustively with benzene. After drying over potash, the 2- [4'-methoxynaphthyl - (I ') - methyl] - imidazole - dihydride (4,5) of the formula
EMI0001.0030
    recrystallized from toluene.



  Instead of 4-methoxy-naphthyl- (1) - acetiminoäthyläther can just as well another ether such. B. the methyl, propyl or butyl ethers are used. Instead of the hydrochloric acid salt of 4-methoxynaphthyl- (1) -acetiminoäthers you can also use another salt, such as. B. from the hydrobromic acid, the sulfuric acid or the methyl sulfuric acid salt.

Claims

PATENT CLAIM: Process for the preparation of a linidazole dihydride (4,5) substituted in the 2-position, characterized in that a 4-methoxy-naphthyl- (1) -acetiminoether is reacted with ethylenediamine. The 2- [4'-methoxy-naphthyl- (1 ') -methyl] -imida7ol-dihydride- (4,5) obtained in this way forms colorless crystals with a melting point of 123 to 124'. Its hydrochloride is a colorless crystal powder from F. 913 to 214. The new compound can be used as a medicine.

SUBJECT DISCLOSURES 1. Process according to claim, characterized in that 4 - methoxy - naphthyl - (1) - acetiminoethyl ether is used for the reaction. 2. The method according to claim, characterized in that a 4-l) lethoxy-naphthyl- (1) -acetimino ether is used for the reaction, which was obtained from a salt of the same. 3.

Process according to claim and claim 2, characterized in that a 4-methogy-iiaplithy 1- (1) -acetiininoether obtained from a hydrohalide thereof is used for the reaction. 4. Method according to claim and the subclaims? and 3, characterized in that a 4-methoxy-naplithyl - (1) - acetimino ether, which was obtained from the hydrochloride of the same, is used for the reaction. 5.

Process according to patent claim and the sub-claims 1 to 4, characterized in that 4-, #letlioxy-naphthyl- (1) -acetiminoethyl ether is used for the reaction, which was obtained from the hydrochloride of the same.