CH204736A - 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
CH204736A
CH204736A CH204736DA CH204736A CH 204736 A CH204736 A CH 204736A CH 204736D A CH204736D A CH 204736DA CH 204736 A CH204736 A CH 204736A
Authority
CH
Switzerland
Prior art keywords
dihydride
imidazole
methyl
hydrochloride
substituted
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 CH204736A publication Critical patent/CH204736A/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-(4,6).            Gegenstand    des vorliegenden Patentes ist  ein Verfahren zur Darstellung     eines    in       2-Stellung    substituierten     Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     p-Methyl-phenylacetimino-          äther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(4'-Methyl-benzyl)-          imidazol-dihydrid-(4,5)        bildet    farblose Kri  stalle. Sein Hydrochlorid ist ein farbloses  Kristallpulver vom F. 206 bis 207  .  



  Die neue Verbindung     kann    als Arznei  mittel verwendet werden.    <I>Beispiel:</I>  2,3 Teile     p-Methyl-phenyl-acetiminoäthyl-          äther-hydrochlorid    der Formel  
EMI0001.0017     
    (hergestellt aus     p-Methyl-phenyl-acetonitril),     aus dem sich während der Umsetzung     p-Me-          thyl-phenylacetiminoäthyläther    bildet, wer-    den in 15 Teilen absolutem Alkohol gelöst.       Man    fügt ziemlich rasch 1 Teil Äthylen  diamin     hinzu,    erhitzt langsam auf<B>100'</B>     und     hält einige Stunden bei dieser Temperatur.

    Hernach vertreibt man den Alkohol, versetzt  den Rückstand mit verdünnter Natronlauge  und extrahiert erschöpfend mit Benzol. Nach  dem Trocknen über Pottasche wird das 2-(4'  Methyl-benzyl)-imidazol-dihydrid-(4,5) der  Formel  
EMI0001.0024     
         in    sein Hydrochlorid übergeführt.  



  An Stelle von     p-Methyl-phenylacetimino-          ä-thyläther    kann ebensogut ein anderer Äther,  wie z. B. der     Methyl-,        Propyl-    oder     Butyl-          äther        Verwendung        finden.     



  Statt vom salzsauren Salz des     p-Methyl-          phenylacetiminoäthers        kann    man auch von  einem andern Salze, wie z. B. vom     bromwas-          serstoffsauren,    vom schwefelsauren oder vom       methylschwefelsauren    Salz ausgehen.



  Process for the preparation of a 2-substituted imidazole dihydride (4,6). The subject of the present patent is a process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, which is characterized in that a p-methylphenylacetimino ether is reacted with ethylenediamine.



  The 2- (4'-methyl-benzyl) - imidazole-dihydride- (4,5) obtained in this way forms colorless crystals. Its hydrochloride is a colorless crystal powder from F. 206 to 207.



  The new compound can be used as a medicine. <I> Example: </I> 2.3 parts of p-methyl-phenyl-acetiminoethyl ether hydrochloride of the formula
EMI0001.0017
    (made from p-methyl-phenyl-acetonitrile), from which p-methyl-phenylacetiminoethyl ether is formed during the reaction, are dissolved in 15 parts of absolute alcohol. 1 part of ethylene diamine is 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 dilute sodium hydroxide solution and extracted exhaustively with benzene. After drying over potash, the 2- (4 'methyl-benzyl) -imidazole-dihydride- (4,5) of the formula
EMI0001.0024
         converted into its hydrochloride.



  Instead of p-methyl-phenylacetimino-ethyl ether, another ether, such as e.g. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of p-methylphenylacetiminoäthers one can also use another salt, such as. B. start with the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in 2-Stel- lung substituierten Imidazoldihydrids-(4,5), dadurch gekennzeichnet, dass man einen p- 3lethyl-phenylacetiminoäther mit Xtby len- diamin umsetzt. Das so gewonnene 2-(4'-illethyl-benzyl)- imidazol-dihydrid-(4,5) bildet farblose Kri stalle. Sein Hydrochlorid ist ein farbloses Kristallpulver vom F. 206 bis 20"r . 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 p-3lethylphenylacetiminoether is reacted with Xtbylenediamine. The 2- (4'-illethyl-benzyl) - imidazole-dihydride- (4,5) obtained in this way forms colorless crystals. Its hydrochloride is a colorless crystal powder with a F. 206 to 20 "r. The new compound can be used as a medicament. SUBClaims: 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung p-Methyl-pheny lacetiminoäthyläther ver wendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen p-Methyl-phenylacetiminoätlier ver- wendet, der aus einem Salz desselben er halten wurde. 3. Verfahren nach Patentanspruch und Un teranspruch ?, dadurch gekennzeichnet, dass man zur Umsetzung einen p-llethyl- phenylacetiniinoä Hier verwendet, der aus einem Hydrolialogenid desselben erhalten wurde. 4. Process according to claim, characterized in that p-methyl-pheny lacetiminoethyl ether is used for the reaction. 2. The method according to claim, characterized in that a p-methyl-phenylacetiminoätlier is used for the reaction, which he obtained from a salt thereof. 3. The method according to claim and sub-claim?, Characterized in that a p-llethyl-phenylacetiniinoä is used here for the implementation, which was obtained from a hydrolialogenide thereof. 4th Verfahren nach Patentanspruch und den Unteransprüchen ? und 3, dadurch ge kennzeichnet, dass plan zur Umsetzung einen p-DTethyl-plienylacetiminoäther ver wendet, der aus dein Hydrochlorid dessel ben erhalten wurde. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung p-Xe- thylphenyl - acetiminoäthyläther verwen det, der aus dem Hydrochlorid desselben erhalten wurde. Method according to patent claim and the subclaims? and 3, characterized in that plan uses a p-DTethyl-plienylacetiminoether for the implementation, which was obtained from the hydrochloride of the same ben. Process according to patent claim and the sub-claims 1 to 4, characterized in that p-Xethylphenyl - acetiminoethyl ether obtained from the hydrochloride of the same is used for the reaction.
CH204736D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204736A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204736T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204736A true CH204736A (en) 1939-05-15

Family

ID=25723389

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204736D CH204736A (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) CH204736A (en)

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