CH204746A - 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.

Info

Publication number
CH204746A
CH204746A CH204746DA CH204746A CH 204746 A CH204746 A CH 204746A CH 204746D A CH204746D A CH 204746DA CH 204746 A CH204746 A CH 204746A
Authority
CH
Switzerland
Prior art keywords
oxy
dihydride
imidazole
reaction
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 CH204746A publication Critical patent/CH204746A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic 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
    • C07D233/20—Heterocyclic 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
    • C07D233/22—Radicals substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     lmidazoldihydrids-(4,ö).       Gegenstand des vorliegenden Patentes ist  eine Verfahren zur     Darstellung    eines in       2-Stellung        substituierten        Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     2-Oxy-phenoxyacetiminoäther     mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(2'-Oxy-phenoxy-          methyl)-imidazoldihydrid-(4,5)    bildet ein  farbloses Hydrochlorid vom F. 239 bis 240'.  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  23 Teile     2-Oxy-phenoxyacetiminoäthyl-          äther-hydrochlorid    der     Formel     
EMI0001.0015     
    (hergestellt aus dem beim Erhitzen von       Brenzcatechinmonobenzyläther    mit     Chlorace-          tonitril    in Aceton und in     Gegenwart    von    Pottasche entstehenden     2-Benzyloxy-phen-          oxyacetonitril    vom F.     921    durch Umsetzung  mit Alkohol und Salzsäure bei Zimmertem  peratur), aus dem sich während der Umset  zung     2-Oxy-phenoxyacetiminoäthyläther    bil  det, werden in absolutem Alkohol gelöst.

    Man fügt ziemlich rasch 6 Teile Äthylen  diamin hinzu, erhitzt langsam auf<B>100'</B> und  hält einige Stunden bei dieser Temperatur.  Beim Abkühlen der Lösung kristallisiert das       2-(2'-Oxy-phenoxymethyl)-imidazoldihydrid-          (4,5)-hydrochlorid    aus. Es besitzt die Formel  
EMI0001.0026     
    An Stelle von     2-Oxy-phenoxyacetimino-          äthyläther    kann ebensogut ein anderer Äther,  wie z. B. der     Methyl-,        Propyl-    oder     Butyl-          äther    Verwendung finden.  



  Statt vom salzsauren Salz des     2-Oxy-          phenoxyacetiminoäthers    kann man auch von      einem andern Salze, wie z. B. vom     brom-          wasserstoffsauren,    vom schwefelsauren oder  vom     methylschwefelsauren    Salz ausgehen.



  Process for the preparation of an imidazole dihydride (4, ö) substituted in the 2-position. 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 2-oxy-phenoxyacetimino ether is reacted with ethylenediamine.



  The 2- (2'-oxy-phenoxymethyl) -imidazole dihydride (4.5) obtained in this way forms a colorless hydrochloride with a melting point of 239 to 240 '.



  The new compound can be used as a medicine.



  <I> Example: </I> 23 parts of 2-oxy-phenoxyacetiminoethyl ether hydrochloride of the formula
EMI0001.0015
    (made from the 2-benzyloxyphenoxyacetonitrile from F. 921, which is formed when pyrocatechol monobenzyl ether is heated with chloroacetonitrile in acetone and in the presence of potash, by reaction with alcohol and hydrochloric acid at room temperature) -Oxy-phenoxyacetiminoäthyläther bil det are dissolved in absolute alcohol.

    6 parts of ethylene diamine are added fairly quickly, heated slowly to <B> 100 '</B> and held at this temperature for a few hours. When the solution cools, the 2- (2'-oxy-phenoxymethyl) -imidazole dihydride (4,5) hydrochloride crystallizes out. It has the formula
EMI0001.0026
    Instead of 2-oxy-phenoxyacetimino ethyl ether, another ether, such as e.g. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 2-Oxy- phenoxyacetiminoäthers you can also use another salt, such as. B. start from the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in ? Stellung substituierten Imidazoldihydrids- (4,5), dadurch gekennzeichnet, dass man einen 2-Oxy-phenoxyacetiminoäther mit Äthylen- diamin umsetzt. Das so gewonnene ?-(,?'-Oxy-plienoxy- methyl) - imidazoldihydrid - (4,5) bildet ein farbloses Hydrochlorid vom F. 239 bis 240 . Die neue Verbindung kann als Arznei mittel verwendet -erden. UNTERANSPRtCHE: 1. PATENT CLAIM: Method for the representation of an in? Position substituted imidazole dihydride (4,5), characterized in that a 2-oxy-phenoxyacetiminoether is reacted with ethylene diamine. The? - (,? '- Oxy-plienoxymethyl) - imidazole dihydride - (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 239 to 240. The new compound can be used as a medicine. SUBClaims: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung 2-Oxy-phenoxyacetiminoäthyläther ver wendet. ?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur U msetzii.ug einen ')-Oxy-phenoxyacetiminoäther ver wendet, der aus einem Salz desselben er halten wurde. 3. Verfahren nach Patentanspruch und Un teranspruch ?, dadurch gekennzeichnet, dass man zur Umsetzung einen 2-Oxy- phenoxyacet;iminoäther verwendet, der aus einem Hydrohalogenid desselben erhalten wurde. 4. Process according to claim, characterized in that 2-oxy-phenoxyacetiminoethyl ether is used for the reaction. ?. Process according to patent claim, characterized in that a ') -oxy-phenoxyacetiminoether is used for U msetzii.ug, which was obtained from a salt thereof. 3. The process as claimed in claim and claim, characterized in that a 2-oxyphenoxyacet, imino ether obtained from a hydrohalide of the same is used for the reaction. 4th Verfahren nach Patentanspruch und den Unteranspriichen ? und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 2-Oxy-phenoxyacetiminoäther ver wendet, der aus dem Hydrochlorid dessel ben erhalten wurde. Verfahren hach Patentanspruch und den 1'iiteranspriiclien 1 bis 4, dadurch gekenn zeichnet, dass inan zur Umsetzung 2-Oxy- phenoxyacetimino5thyl5ther verwendet, der aus dem Hydrochlorid desselben er halten wurde. Procedure according to the patent claim and the sub-claims? and 3, characterized in that a 2-oxy-phenoxyacetiminoether is used for the reaction, which was obtained from the hydrochloride of the same ben. Process according to patent claim and claims 1 to 4, characterized in that 2-oxyphenoxyacetimino-ethyl ether obtained from the hydrochloride of the same is used for the reaction.
CH204746D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204746A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204746T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204746A true CH204746A (en) 1939-05-15

Family

ID=25723399

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204746D CH204746A (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) CH204746A (en)

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