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

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

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Publication number
CH204729A
CH204729A CH204729DA CH204729A CH 204729 A CH204729 A CH 204729A CH 204729D A CH204729D A CH 204729DA CH 204729 A CH204729 A CH 204729A
Authority
CH
Switzerland
Prior art keywords
reaction
ether
dihydride
same
hydrochloride
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH204729A publication Critical patent/CH204729A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/22Radicals substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

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 (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in ? Stellung substituierten Imidazoldiliydrids- (4,5), dadurch gekennzeichnet, dass man. einen 3,4 -141ethy lendioxyphenylacetiniino- äther mit Äthylendiamin umsetzt. Das so gewonnene \?-( 3',4'-@Iethy@endioxy- benzyl)-imida.zoldihydrid-(4,5) bildet farb lose Kristalle vom F. 114 bis<B>116</B> . Sein Hydrochlorid ist ein farbloses Kristallpulver vom F. ?0? bis \?Ü3 . 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. Die neue Verbindung kann als Arznei mittel verwendet werden. UNTERANSPRÜUCHE: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, da.ss man zur Umsetzung 3,4 - Methylendioxyphenylacetiminoäthyl- äther verwendet. 2. Verfahren nach Patentanspruch, dadurch bekennzeicliiiet, dass man zur Umsetzung einen 3,4-Methylendioxy phenylaeetimino- ätlier verwendet, der aus einem Salz des selben erhalten wurde. 3. 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. Verfahren nach Patentanspruch und Un teranspruch ?, dadurch gekennzeichnet, dass man zur L: msetzung einen 3,4-Me- thylendioxyplienS-lacetiminoäther verwen det, der aus einem Hydrohalobenid des selben erhalten wurde. 4. Verfahren nach Patentanspruch und den Unteransprüchen ? und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 3.4-:llethy lendioxyplienylacetimino- äther verwendet, der aus dem Hydrochlo- rid desselben erhalten wurde. <B>5</B>. 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>. Verfahren nach Patentanspruch und den Unteranspriichen 1 bis 4, dadurch ge kennzeichnet, dass man zur Umsetzung 3,4 - Methylendioxy phenylacetiminoäthyl- ä.ther verwendet, der aus dem Hydro- chlorid desselben erhalten wurde. 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.
CH204729D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204729A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204729T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204729A true CH204729A (en) 1939-05-15

Family

ID=25723382

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204729D CH204729A (en) 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.

Country Status (1)

Country Link
CH (1) CH204729A (en)

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