CH204744A - 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
CH204744A
CH204744A CH204744DA CH204744A CH 204744 A CH204744 A CH 204744A CH 204744D A CH204744D A CH 204744DA CH 204744 A CH204744 A CH 204744A
Authority
CH
Switzerland
Prior art keywords
reaction
dihydride
ether
imidazole
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 CH204744A publication Critical patent/CH204744A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

       

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     Imidazoldibydrids-(4,5).       Gegenstand des vorliegenden Patentes ist  eine Verfahren zur Darstellung eines in       2-Stellung    substituierten     Imidazol-dihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     4-Methoxy-phenoxyacetimino-          äther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(4'-Methoxy-phen-          oxymethyl)-imidazol-dihydrid-(4,5)    bildet  ein farbloses Hydrochlorid vom F. 89 bis  90  , kristallwasserhaltig.  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  24,5 Teile     4-1Vlethoxy-phenoxyacetimino-          äthyläther-hydrochlorid    der Formel  
EMI0001.0013     
    (hergestellt aus dem beim Erhitzen von     Hy-          drochinonmonomethyläther    mit     Chloraceto-          nitril    in     Acetonlösung    und Gegenwart von    Pottasche entstehenden     4-Methoxy-phenogy-          aeetonitril,        gp;,    140 bis 145  ), aus dem sich  während der Umsetzung     4-Methoxy-phenoxy-          acetiminoäthyläther    bildet, werden in abso  lutem Alkohol gelöst.

   Man fügt ziemlich  rasch 6 Teile     Äthylendiamin    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 extrahiert erschöpfend  mit Benzol. Nach dem Trocknen über Pott  asche und     nachherigem    Vertreiben des Ben  zols bleibt das 2 - (4'-     Methoxy    -     phenoxy-          methyl)-imidazoldihydrid-(4,5)    der Formel  
EMI0001.0030     
    zurück.  An Stelle von     4-Methoxy-phenoxyacet-          iminoäthyläther        kann    ebensogut ein anderer  Äther, wie z.

   B. der     Methyl-,        Propyl-    oder       Butyläther    Verwendung finden.      Statt vom salzsauren Salz des     4-Me-          thoxy    -     phenoxyacetiminoäthers    kann man  auch von einem     andern    Salze, wie z. B. vom       bromwasserstoffsauren,    vom schwefelsauren  oder vom     methylschwefelsauren    Salz aus  gehen.



  Process for the preparation of an imidazole dibydride (4,5) 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 4-methoxyphenoxyacetimino ether is reacted with ethylenediamine.



  The 2- (4'-methoxyphenoxymethyl) imidazole dihydride (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 89 to 90, containing water of crystallization.



  The new compound can be used as a medicine.



  <I> Example: </I> 24.5 parts of 4-1Vlethoxyphenoxyacetimino ethyl ether hydrochloride of the formula
EMI0001.0013
    (produced from the 4-methoxyphenogy- aeetonitrile formed when hydroquinone monomethyl ether is heated with chloroacetonitrile in acetone solution and the presence of potash, gp ;, 140 to 145), from which 4-methoxyphenoxyacetiminoethyl ether is formed during the reaction forms are dissolved in absolute alcohol.

   6 parts of ethylenediamine 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 extracted exhaustively with benzene. After drying over pot ash and then driving off the benzene, the 2 - (4'-methoxyphenoxymethyl) imidazole dihydride (4,5) of the formula remains
EMI0001.0030
    back. Instead of 4-methoxy-phenoxyacet- iminoäthyläther, another ether, such as.

   B. the methyl, propyl or butyl ethers are used. Instead of the hydrochloric acid salt of 4-methoxy - phenoxyacetiminoether 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)

PATENTANSPRUCH: Verfahren zur Darstellung eines in ? Stellung substitutierten Imidazoldihydrids- (4,5), dadurch gekennzeichnet, dass man einen 4-illethoxy-phenoxyacetiminoäther finit Äthylendiamin umsetzt. Das so gewonnene 2-(4'-Methoxy-phen- oxymethyl)-imidazol-dihydrid-(4,5) bildet ein farbloses Hydrochlorid vom F. 89 bis<B>90</B> kristallwasserhaltig. Die neue Verbindung kann als Arznei mittel verwendet werden. UNTERANSPRüCFIE 1. PATENT CLAIM: Method for the representation of an in? Position substituted imidazole dihydride (4,5), characterized in that a 4-illethoxy-phenoxyacetiminoether is converted finitely ethylenediamine. The 2- (4'-methoxyphenoxymethyl) imidazole dihydride (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 89 to 90, containing water of crystallization. The new compound can be used as a medicine. SUBCLAIM 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung 4 - Methoxy - phenoxyacetiminoäthylätlier verwendet. ?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen 4-1lethoxy-phenoxyacetiminoäther verwendet, der aus einem Salz desselben erhalten wurde. 3. Verfahren nach Patentansprueh und Un teranspruch ?, dadurch gekennzeichnet, da13 man zur Umsetzung einen 4-Methoxy- phenoxyacetiminoäther verwendet, der aus einem Hydrolialogenid desselben erhalten wurde. 4. Process according to patent claim, characterized in that 4-methoxyphenoxyacetiminoethyl ether is used for the reaction. ?. Process according to patent claim, characterized in that a 4-1lethoxy-phenoxyacetimino ether is used for the reaction, which was obtained from a salt thereof. 3. The method according to patent claim and sub-claim?, Characterized in that a 4-methoxyphenoxyacetiminoether is used for the reaction, which was obtained from a hydrolialogenide of the same. 4th Verfahren nach Patentanspruch und den U nteranspriichen 2 und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 4-Dlethoxy-plienoxyacetiminoäther verwendet, der aus dem Hydrochlorid des selben erhalten wurde. 5. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung 4-lTe- tlioxy-phenoxyacetiminoäthyläther verv-en- det, der aus dein Hydrochlorid desselben erhalten wurde. Process according to patent claim and subclaims 2 and 3, characterized in that a 4-di-ethoxy-plienoxyacetimino ether obtained from the hydrochloride of the same is used for the reaction. 5. The method according to claim and the subclaims 1 to 4, characterized in that 4-l-tetlioxy-phenoxyacetiminoethyl ether obtained from the hydrochloride of the same is used for the reaction.
CH204744D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204744A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204744T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204744A true CH204744A (en) 1939-05-15

Family

ID=25723397

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204744D CH204744A (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) CH204744A (en)

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