CH204741A - 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
CH204741A
CH204741A CH204741DA CH204741A CH 204741 A CH204741 A CH 204741A CH 204741D A CH204741D A CH 204741DA CH 204741 A CH204741 A CH 204741A
Authority
CH
Switzerland
Prior art keywords
ethoxy
dihydride
hydrochloride
substituted
ver
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 CH204741A publication Critical patent/CH204741A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     Imidazoldihydrids-(4,ö).       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     2-Athoxy-phenoxyacetimino-          äther    mit     Athylendiamin    umsetzt.  



  Das so gewonnene     2-(2'-Äthoxy-phenoxy-          methyl)-imidazol-dihydrid-(4,5)    bildet ein  farbloses Hydrochlorid vom F. 138 bis 139  .  



  Die neue Verbindung     kann    als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>       22   <B>6</B>     Teile    2 -     Äthoxy    -     phenoxyacetimino-          äthyläther-hydrochlorid    der Formel  
EMI0001.0017     
    (hergestellt aus dem beim Erhitzen von     Gu-          äthol    mit     Chloracetonitril    in     Acetonlösung       und Gegenwart von     Pottasche    entstehenden  2 -     Äthoxy    -     phenoxyacetonitril,        Kp4    125  ,  F.

   44  ), aus dem sich während der Umset  zung     2-Athoxy-phenoxyacetiminoäthyläther     bildet, werden in absolutem Alkohol gelöst.  Man fügt ziemlich rasch 6 Teile     Athylen-          diamin    hinzu, erhitzt langsam auf<B>100'</B> und  hält einige Stunden bei dieser Temperatur.  Hernach vertreibt man den Alkohol, versetzt  den Rückstand mit Natronlauge und extra  hiert erschöpfend mit Benzol. Nach dem       Trocknen    über Pottasche     und        nachherigem     Vertreiben des Benzols bleibt das     2-(2'-Athoxy-          phenoxymethyl)-imidazoldihydrid-(4,5)    der  Formel  
EMI0001.0034     
    zurück.

    An Stelle von 2 -     Äthoxy-        phenoxyacet-          iminoäthyläther    kann ebensogut ein anderer           -lther,    wie z. B. der     Methyl-,        Propyl-    oder       Butyläther    Verwendung finden.  



  Statt vom salzsauren Salz des     2-Ällioxy-          plienoxyacetiminoä.thers    kann man auch von  einem andern Salze, wie z. B. vom     bromwas-          serstoffsauren,    vom     schwefelsauren    oder vom       inethylscliwefelsauren    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) substituted in the 2-position, which is characterized in that a 2-ethoxy-phenoxyacetimino ether is reacted with ethylenediamine.



  The 2- (2'-ethoxyphenoxymethyl) imidazole dihydride (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 138 to 139.



  The new compound can be used as a medicine.



  <I> Example: </I> 22 <B> 6 </B> parts 2 - ethoxy - phenoxyacetimino ethyl ether hydrochloride of the formula
EMI0001.0017
    (made from the 2-ethoxy-phenoxy-acetonitrile formed when guethol is heated with chloroacetonitrile in acetone solution and in the presence of potash, Kp4 125, F.

   44), from which 2-ethoxy-phenoxyacetiminoethyl ether is formed during the implementation, 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. The alcohol is then driven off, the residue is mixed with sodium hydroxide solution and then exhaustively with benzene. After drying over potash and subsequent driving off of the benzene, the 2- (2'-ethoxyphenoxymethyl) imidazole dihydride (4,5) of the formula remains
EMI0001.0034
    back.

    Instead of 2 - ethoxyphenoxyacet iminoäthyläther can just as well another ether, such as z. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 2-Ällioxy- plienoxyacetiminoä.thers one can also use another salt, such as z. B. from the hydrobromic acid, from the sulfuric acid or from the methylsulfuric acid salt.

Claims (1)

PATEN TAN SPRUCH Verfahren zur Darstellung eines in 2-Stel- lung substituierten Imida.zoldihy diids-(,4,5), dadurch gekennzeichnet dass man einen 2- Ätlioxy-phenoxya.cetiminoäther mit Äthylen- diaiiiin umsetzt. Pas so gewonnene 2-(2' Äthoxy-phenoxy- metlhyl)-imida.zol-dihydrid-(4,5) PATEN TAN SPRUCH Process for the preparation of an Imida.zoldihy diids substituted in the 2-position - (, 4,5), characterized in that a 2-Ätlioxy-phenoxya.cetiminoäther is reacted with Äthylen- diaiiiin. The 2- (2 'ethoxy-phenoxy-methyl) -imida.zol-dihydride- (4,5) obtained in this way bildet ein farbloses Hydrochlorid vom F.<B>1.38</B> bis<B>1.39</B> ". Die neue Verbindung kann als Arznei mittel verwendet werden. UN TERAN SPM CHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, da.ss man zur Umsetzung 2-Äthoxy-phenoxyacetiminoäthyläther ver wendet. forms a colorless hydrochloride from F. <B> 1.38 </B> to <B> 1.39 </B> ". The new compound can be used as a medicament. UN TERAN SPM CHE 1. Process according to patent claim, characterized in that .ss to implement 2-ethoxy-phenoxyacetiminoäthyläther ver used. -?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, da-ss man zur Umsetzung einen ? - Xtlioxy - phenoxy aeetiminoäther ver -endet, der aus einem Salz desselben erhalten wurde. 2. - ?. Method according to patent claim, characterized in that a? - Xtlioxy - phenoxy aeetiminoäther ver -endet, which was obtained from a salt thereof. 2. Verfahren nach Patentanspruch und Un teranspruch 2, dadurch gekennzeichnet, dass man zur Umsetzung einen 2-Äthoxy- plienoxyaoetimiiloätlier verwendet, der aus eineng .1-Iydrohalogenid desselben erhalten will-de. 4. Verfahren nach. Patentanspruch und den Unteransprüchen ? und 3, dadurch gekenn zeichnet, da.ss man zur Umsetzung einen ?-Äthoxy-phenoxyacetiminoäther verwen det, der aus dem IHydrochlorid desselben erhalten wurde. Process according to patent claim and sub-claim 2, characterized in that a 2-ethoxy-plienoxyaoetimiiloätlier is used for the reaction, which wants to obtain the same from a .1-hydrohalide thereof. 4. Procedure according to. Claim and the subclaims? and 3, characterized in that a? -ethoxy-phenoxyacetiminoether is used for the reaction, which was obtained from the hydrochloride of the same. Verfahren nach Patentanspruch und den U nteranspriiehen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung ? Äthoxy-phenoxyacetiminoäthyläther ver wendet. der aus dem Hvdrochlorid dessel ben erhalten wurde. Method according to patent claim and subclaims 1 to 4, characterized in that one can implement? Ethoxy-phenoxyacetiminoäthyläther used ver. which was obtained from the hydrochloride of the same ben.
CH204741D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204741A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204741T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204741A true CH204741A (en) 1939-05-15

Family

ID=25723394

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204741D CH204741A (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) CH204741A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2401142A1 (en) * 1976-12-20 1979-03-23 Wellcome Found IMIDAZOLINE DERIVATIVES AND THEIR PREPARATION

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2401142A1 (en) * 1976-12-20 1979-03-23 Wellcome Found IMIDAZOLINE DERIVATIVES AND THEIR PREPARATION

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