CH204743A - 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
CH204743A
CH204743A CH204743DA CH204743A CH 204743 A CH204743 A CH 204743A CH 204743D A CH204743D A CH 204743DA CH 204743 A CH204743 A CH 204743A
Authority
CH
Switzerland
Prior art keywords
isopropyl
methyl
reaction
ethyl
dihydride
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 CH204743A publication Critical patent/CH204743A/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

Description

  

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     Imidazoldihydrids-(4,6).       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung eines     iri          2-Stellung    substituierten     Imidazol-dihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     3-Methyl-6-isopropyl-phen-          oxyacetiminoäther    mit     Äthylendiamin    um  setzt.  



  Das so gewonnene     2-(3')-Methyl-6'-isopro-          pyl        -phenoxymethyl)    -     imidazoldihydrid    44,5)  bildet ein farbloses Hydrochlorid vom F. 215  bis 217  .  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  27 Teile     3-Methyl-6-isopropyl-phenoxy-          acetiminoäthyläther-hydrochlorid    der Formel  
EMI0001.0016     
    (hergestellt aus dem beim Erhitzen von     Thy-          mol    mit     Chloracetonitril    in     Acetonlösung    und  Gegenwart von Pottasche entstehenden     3-          Methyl-6-isopropyl-phenoxyacetonitril,        gp        o,4     114 bis<B>118'),</B> aus dem sich während der  Umsetzung     3-Methyl-6-isopropyl-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     Glas    2 - (3'     -Methyl-        6'-isopropyl-          phenoxymethyl)-imidazoldihydrid-(4,5)

      der  Formel  
EMI0001.0034     
      An Stelle von     3-llethyl-6-isopropy        1-phen-          oxyacetiminoäthyläther    kann ebensogut ein  anderer Äther, wie z. B. der     Methyl-,        Pro-          pyl-    oder     Butyläther    Verwendung finden.  



  Statt vom salzsauren Salz des     3-Methyl-          6    -     isopropyl    -     plienoxyacetiminoäthei-s    kann  man auch von einem andern Salze, wie z. B.  vom     bromwasserstoffsauren,    vom schwefel  sauren oder vom     methvlschwefelsauren    Salz  ausgehen.



  Process for the preparation of a 2-substituted imidazole dihydride (4,6). 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 3-methyl-6-isopropyl-phenoxyacetiminoether is reacted with ethylenediamine.



  The 2- (3 ') - methyl-6'-isopropyl-phenoxymethyl) - imidazole dihydride 44.5) obtained in this way forms a colorless hydrochloride with a melting point of 215 to 217.



  The new compound can be used as a medicine.



  <I> Example: </I> 27 parts of 3-methyl-6-isopropyl-phenoxy-acetiminoethyl ether hydrochloride of the formula
EMI0001.0016
    (produced from the 3-methyl-6-isopropyl-phenoxyacetonitrile formed when thymol is heated with chloroacetonitrile in acetone solution and the presence of potash, gp 0.414 to 118 '), </B> from which during the reaction forms 3-methyl-6-isopropyl-phenoxy-acetiminoethyl ether, are dissolved in abso lutem 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, glass 2 remains - (3'-methyl- 6'-isopropyl-phenoxymethyl) -imidazole dihydride- (4.5)

      the formula
EMI0001.0034
      Instead of 3-llethyl-6-isopropy 1-phenoxyacetiminoethyl ether, another ether, such as e.g. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 3-methyl- 6 - isopropyl - plienoxyacetiminoäthei-s you can also use another salt, such as. B. from the hydrobromic acid, from the sulfuric acid or from the methosulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in ?-Stel lung substituierten Iniidazoldihydrids-(.4,5), dadurch gekennzeichnet, dass man einen 3- 1lethyl - 6 - isopropyl -phenoxy acetiminoäther mit ithylendiamin umsetzt. PATENT CLAIM: Process for the preparation of an iniidazole dihydride substituted in? -Position - (. 4,5), characterized in that a 3- 1-ethyl-6-isopropyl-phenoxy acetiminoether is reacted with ethylenediamine. Das so gewonnene ?-(3'-lIethyl-6'-isopro- pyl-phenoxymethy 1) - imidazol-dihy drill -(4,5 bildet ein farbloses Hydrochlorid vom F. 915 bis<B>2</B>17 . Die neue Verbindung kann als Arznei mittel verwendet werden. UNTERAN SPRüCHE 1. The? - (3'-ethyl-6'-isopropyl-phenoxymethy 1) - imidazole-dihy drill - (4,5 forms a colorless hydrochloride from F. 915 to <B> 2 </B> 17. The new compound can be used as a medicinal product. SUB-APPROACH 1. Verfahren nach Patenta.nspriich, dadurch gekennzeichnet, dass man zur Umsetzung 3 -Methyl -1> - isopropyl -hhenoxy acetimino- äthylätlier verwendet. ?. Verfahren nach Patentanspruch, dadurch geli#ennzei.chnet, dass man zur Umsetzung einen 3 - Dlethyl-6-isopropyl - phenoxyacet- iniinoäther verwendet, der aus einem Salz desselben erhalten wurde. 3. Process according to patent claim, characterized in that 3-methyl-1> -isopropyl-phenoxy acetimino-ethyl ether is used for the reaction. ?. Process according to patent claim, characterized in that a 3-methyl-6-isopropyl-phenoxyacetinoether obtained from a salt thereof is used for the reaction. 3. Verfahren nach Patentanspruch und Un teranspruch 2, dadurch gekennzeichnet, dass man zur Umsetzung einen 3-3tethyl- 6-isopropyl-phenoxyacetiminoäther ver wendet, der aus einem Hydrohalogenid desselben erhalten wurde. 4. Verfahren nach Patentanspruch und den Unteranspriichen \? und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 3-blethy 1-6-isopropyl-phenoxyacet- iminoäther verwendet, der aus dem Hi-- drochlorid desselben erhalten wurde. Process according to patent claim and un teran claim 2, characterized in that a 3-3-ethyl-6-isopropyl-phenoxyacetiminoether is used for the reaction, which was obtained from a hydrohalide thereof. 4. Procedure according to patent claim and the subclaims \? and 3, characterized in that a 3-methyl 1-6-isopropyl-phenoxyacetiminoether is used for the reaction, which was obtained from the hydrochloride of the same. :@. Verfahren naeh Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung 3-i11e thyl-6-isopropyl-phenoxyacetiminoäthyl- ätlier verwendet, der aus dem Hydrochlo- rid desselben erhalten wurde. : @. A method according to patent claim and the dependent claims 1 to 4, characterized in that 3-i11e-ethyl-6-isopropyl-phenoxyacetiminoethyl ether obtained from the hydrochloride thereof is used for the reaction.
CH204743D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204743A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204743T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204743A true CH204743A (en) 1939-05-15

Family

ID=25723396

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204743D CH204743A (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) CH204743A (en)

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