CH204729A

CH204729A - Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.

Info

Publication number: CH204729A
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     Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     3,4-Methylendioxyphenylacet-          iminoäther    mit     Äthylendiamin    umsetzt.  



  Das so     gewonnene        2-(3',4'-Methylendioxy-          benzyl)-imidazoldihydrid-(4,5)    bildet farb  lose     Kristalle    vom F. 114 bis 116  . Sein  Hydrochlorid ist ein farbloses Kristallpul  ver vom F. 202 bis 203  .  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  3,4 -     Methylendioxyphenylacetiminoäthyl-          äther-hydrochlorid    der Formel  
EMI0001.0017     
    (hergestellt aus 1,7 Teilen 3,4-Methylen-         dioxyphenylacetonitril),    aus dem sich wäh  rend der Umsetzung     3,4-Methylendioxyphe-          nylacetiminoäthyläther    bildet, wird in 13 Tei  len absolutem Alkohol gelöst. Man fügt  ziemlich rasch 1 Teil     Äthylendiamin        hinzu,     erhitzt langsam auf<B>100</B>   und hält einige  Zeit bei dieser Temperatur. Hernach ver  treibt man den Alkohol, versetzt den Rück  stand bei guter Eiskühlung     mit    Natronlauge  und extrahiert erschöpfend mit Benzol.

   Nach  dem     Trocknen    über Pottasche wird das Ben  zol vertrieben. Es     hinterbleibt    kristallisier  tes 2 - (3',4'-     Methylendiogybenzyl)    -     imidazol-          dihydrid-(4,5)    der     Formel     
EMI0001.0030     
    An Stelle von     3,4-Methylendioxyphenyl-          aeetiminoäthyläther    kann ebensogut ein an  derer Äther, wie z. B. der     Methyl-,        Propyl-          oder        Butyläther    Verwendung finden.

             Statt    vom salzsauren Salz des     3,4-1ie-          thylendioxyphenylacetiminoäthers    kann man  auch von einem andern Salze, wie z. B. vom       bromwasserstoffsauren,    vom schwefelsauren  oder vom     methy        lschwefelsauren    Salz aus  gehen.



  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 3,4-methylenedioxyphenylacetiminoether is reacted with ethylenediamine.



  The 2- (3 ', 4'-methylenedioxybenzyl) imidazole dihydride (4,5) obtained in this way forms colorless crystals with a melting point of 114 to 116. Its hydrochloride is a colorless crystal powder with a melting point of 202 to 203.



  The new compound can be used as a medicine.



  <I> Example: </I> 3,4 - methylenedioxyphenylacetiminoethyl ether hydrochloride of the formula
EMI0001.0017
    (made from 1.7 parts of 3,4-methylenedioxyphenylacetonitrile), from which 3,4-methylenedioxyphenyl acetiminoethyl ether is formed during the reaction, is dissolved in 13 parts of absolute alcohol. 1 part ethylenediamine is added fairly quickly, heated slowly to <B> 100 </B> and held at this temperature for some time. The alcohol is then driven off, the residue is mixed with sodium hydroxide solution with good ice cooling and extracted exhaustively with benzene.

   After drying over potash, the benzene is sold. Crystallized 2 - (3 ', 4'-methylenediogybenzyl) - imidazole dihydride (4,5) of the formula remains
EMI0001.0030
    Instead of 3,4-methylenedioxyphenyl aeetiminoäthyläther can just as well another ether such. B. the methyl, propyl or butyl ethers are used.

             Instead of the hydrochloric acid salt of 3,4-1ie- thylendioxyphenylacetiminoäthers you can also use another salt, such as. B. from the hydrobromic acid, from the sulfuric acid or from the methy lsulfuric acid salt.

Claims

PATENT CLAIM: Method for the representation of an in? Position substituted imidazole dihydride (4,5), characterized in that one. a 3,4 -141ethy lendioxyphenylacetiniino- ether with ethylenediamine is reacted. The \? - (3 ', 4' - @ Iethy @ endioxy-benzyl) -imida.zoldihydride- (4,5) obtained in this way forms colorless crystals from F. 114 to <B> 116 </B>. Its hydrochloride is a colorless crystal powder from F.? 0? until \? Ü3.

The new compound can be used as a medicine. SUBClaims: 1. Process according to claim, characterized in that the reaction is 3,4 - methylenedioxyphenylacetiminoethyl ether used. 2. The method according to claim, characterized in that a 3,4-Methylendioxy phenylaeetimino- ätlier is used for the reaction, which was obtained from a salt of the same. 3.

Process according to patent claim and sub-claim?, Characterized in that a 3,4-methylenedioxypliene-lacetiminoether is used for the L: reaction, which was obtained from a hydrohalobide of the same. 4. Method according to claim and the subclaims? and 3, characterized in that a 3,4-: llethy lendioxyplienylacetimino- ether is used for the reaction, which was obtained from the hydrochloride of the same. <B> 5 </B>.

Process according to patent claim and sub-claims 1 to 4, characterized in that 3,4-methylenedioxy phenylacetiminoethyl ether obtained from the hydrochloride of the same is used for the reaction.