CH204742A - 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
CH204742A
CH204742A CH204742DA CH204742A CH 204742 A CH204742 A CH 204742A CH 204742D A CH204742D A CH 204742DA CH 204742 A CH204742 A CH 204742A
Authority
CH
Switzerland
Prior art keywords
dihydride
imidazole
substituted
preparation
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 CH204742A publication Critical patent/CH204742A/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        sabstituierten        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     Phenoxyacetiminoäther    mit       Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(Phenoxymethyl)-          imidazol-dihydrid-(4,5)    bildet ein farbloses  Hydrochlorid vom F. 130 bis<B>132'.</B>  



  Die neue Verbindung kann als Arznei  mittel     verwendet    werden.  



  <I>Beispiel:</I>  21 Teile     Phenoxyacetiminoäthyläther-hy-          drochlorid    der Formel  
EMI0001.0015     
    aus dem sich während der Umsetzung     Phen-          oxyacetiminoäthyläther    bildet, werden in ab  solutem Alkohol gelöst. Man fügt ziemlich  rasch 6 Teile     Äthylendiamin    hinzu, erhitzt    langsam auf 100   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 Pottasche  und     nachherigem    Vertreiben des Benzols  bleibt das     2-(Phenoxymethyl)-imidazoldihy-          drid-(4,5)    der Formel  
EMI0001.0022     
    zurück.  An Stelle von     Phenoxyacetiminoäthyl-          äther    kann ebensogut ein anderer Äther, wie  z. B. der     Methyl-,        Propyl-    oder     Butyläther     Verwendung finden.  



       Statt    vom salzsauren Salz des     Phenoxy-          acetiminoäthers    kann man auch von einem  andern Salze, wie z. B. vom     bromwasser-          stoffsauren,    vom schwefelsauren oder vom       methylschwefelsauren    Salz ausgehen.



  Process for the preparation of an imidazole dihydride (4, 6) 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 phenoxyacetimino ether is reacted with ethylenediamine.



  The 2- (phenoxymethyl) -imidazole-dihydride- (4,5) obtained in this way forms a colorless hydrochloride with a temperature of 130 to 132 '



  The new compound can be used as a medicine.



  <I> Example: </I> 21 parts of phenoxyacetiminoethyl ether hydrochloride of the formula
EMI0001.0015
    from which phenoxyacetiminoethyl ether is formed during the reaction, are dissolved in ab solute alcohol. 6 parts of ethylenediamine are added fairly quickly, heated slowly to 100 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 potash and then driving off the benzene, the 2- (phenoxymethyl) imidazole dihydride (4,5) of the formula remains
EMI0001.0022
    back. Instead of Phenoxyacetiminoäthyl- ether, another ether, such as z. B. the methyl, propyl or butyl ethers are used.



       Instead of the hydrochloric acid salt of the phenoxy acetiminoether one can also use another salt, such as B. from the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in 2 Stellung substituierten Imidazoldiliydrids- (4,5), dadurch gekennzeichnet, dass man einen Phenoxyacetiminoäther mit Ät.hylen- diamin umsetzt. Steltung substituierten Imidazoldihydrids- imidazol-dihydrid-(4,5) bildet ein farbloses Hydrochlorid vom F. 130 bis<B>13-)</B> . Die neue Verbindung kann als Arznei mittel verwendet werden. UNTERANSPRüCHE: 1. PATENT CLAIM: Process for the preparation of an imidazole dihydride (4,5) substituted in the 2 position, characterized in that a phenoxyacetiminoether is reacted with Ät.hylen- diamine. Substituted imidazole dihydride- imidazole-dihydride- (4,5) forms a colorless hydrochloride from F. 130 to <B> 13-) </B>. The new compound can be used as a medicine. SUBCLAIMS: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung Phenoxyacetiminoäthyläther verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen Phenoxy acetiminoäther verwendet, der aus einem Salz desselben erhalten wurde. 3. Verfahren nach Patentanspruch und Un teranspruch ?, dadurch gekennzeichnet, dass mau zur Umsetzung einen Phenoxy- acetiminoätlier verwendet, der aus einem Hydrohalogenid desselben erhalten wurde. 4. Process according to patent claim, characterized in that phenoxyacetiminoethyl ether is used for the reaction. 2. The method according to claim, characterized in that a phenoxy acetiminoether is used for the reaction, which was obtained from a salt thereof. 3. The method according to claim and sub-claim?, Characterized in that a Phenoxy- acetiminoätlier is used for the implementation, which was obtained from a hydrohalide of the same. 4th Verfahren nach Patentanspruch und den Unteransprüchen 2 und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen Plienoxyacetiminoäther verwendet, der aus dem Hydrochlorid desselben er halten wurde. 5. Verfahren nach Patentanspruch und den U nteranspriicben l bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung Phen- oxyacetiminoäthy hither verwendet, der aus dem Hydrochlorid desselben erhalten wurde. A method according to claim and the dependent claims 2 and 3, characterized in that a Plienoxyacetiminoäther is used for the implementation, which was obtained from the hydrochloride of the same. 5. The method according to patent claim and the sub-claims 1 to 4, characterized in that phenoxyacetiminoethylene is used for the reaction, which is obtained from the hydrochloride of the same.
CH204742D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204742A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204742T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204742A true CH204742A (en) 1939-05-15

Family

ID=25723395

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204742D CH204742A (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) CH204742A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3449354A (en) * 1967-04-04 1969-06-10 Dow Chemical Co 2-((2-trifluoromethylphenoxy)methyl)-2-imidazoline
US3449357A (en) * 1967-04-04 1969-06-10 Dow Chemical Co 2-((2,6-substituted)phenoxymethyl)-2-imidazolines
US3449356A (en) * 1967-04-04 1969-06-10 Dow Chemical Co 2-((halophenoxy)methyl)-2-imidazolines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3449354A (en) * 1967-04-04 1969-06-10 Dow Chemical Co 2-((2-trifluoromethylphenoxy)methyl)-2-imidazoline
US3449357A (en) * 1967-04-04 1969-06-10 Dow Chemical Co 2-((2,6-substituted)phenoxymethyl)-2-imidazolines
US3449356A (en) * 1967-04-04 1969-06-10 Dow Chemical Co 2-((halophenoxy)methyl)-2-imidazolines

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