CH204727A - 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
CH204727A
CH204727A CH204727DA CH204727A CH 204727 A CH204727 A CH 204727A CH 204727D A CH204727D A CH 204727DA CH 204727 A CH204727 A CH 204727A
Authority
CH
Switzerland
Prior art keywords
reaction
process according
substituted
hydrochloride
preparation
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 CH204727A publication Critical patent/CH204727A/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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     Imidazoldihydrids-(4,5).       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     4-Methoxyphenylacetimino-          äther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(4'-Methoxybenzyl)-          imidazol-dihydrid-(4,5)    bildet farblose Kri  stalle vom F. 118 bis 120'. Sein     Hydrochlo-          rid    ist ein farbloses Kristallpulver.  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>       4-Methoxyphenylacetiminoäthyläther-hy-          drochlorid    der Formel  
EMI0001.0015     
    (hergestellt aus 1,4 Teilen     4-Methoxyphenyl-          a.cetonitril),    aus dem sich während der Um  setzung 4 - Methoxyphenylacetiminoäthyl-         äther    bildet, wird in 12 Teilen absolutem  Alkohol gelöst. Man fügt ziemlich rasch  1 Teil     Äthylendiamin    hinzu, erhitzt langsam  auf<B>100'</B> und hält einige     Stunden    bei dieser  Temperatur.

   Hernach vertreibt man den Al  kohol, versetzt den Rückstand bei guter Eis  kühlung mit Natronlauge, wobei das     2-(4'-          Methoxy-benzyl)-imidazoldihydrid-(4,5)    der  Formel  
EMI0001.0023     
    auskristallisiert. Es wird nach dem Trock  nen aus     Toluol    umkristallisiert.  



  An Stelle von     4-Methoxyphenylacetimino-          äthyläther    kann ebensogut ein anderer Äther,  wie z. B. der     Methyl-,        Propyl-    oder     Butyl-          äther    Verwendung finden.  



  Statt vom salzsauren Salz des     4-Methoxy-          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 an imidazole dihydride (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-methoxyphenylacetimino ether is reacted with ethylenediamine.



  The 2- (4'-methoxybenzyl) - imidazole-dihydride- (4,5) obtained in this way forms colorless crystals with a melting point of 118 to 120 '. Its hydrochloride is a colorless crystal powder.



  The new compound can be used as a medicine.



  <I> Example: </I> 4-methoxyphenylacetiminoethyl ether hydrochloride of the formula
EMI0001.0015
    (made from 1.4 parts of 4-methoxyphenyl a.cetonitrile), from which 4 - methoxyphenylacetiminoethyl ether is formed during the reaction, is dissolved in 12 parts of absolute alcohol. 1 part ethylenediamine is added fairly quickly, heated slowly to <B> 100 '</B> and held at this temperature for a few hours.

   The alcohol is then sold, the residue is treated with sodium hydroxide solution while cooling well with ice, the 2- (4'-methoxy-benzyl) -imidazole dihydride (4.5) of the formula
EMI0001.0023
    crystallized out. After drying it is recrystallized from toluene.



  Instead of 4-Methoxyphenylacetimino- äthyläther, another ether, such as z. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 4-Methoxyphenylacetiminoäthers you can also use another salt, such as. B. start with the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims (1)

PATENTAN SPRUCI3 Verfahren zur Darstellung eines in 2 Stellung substituierten Imidazoldihy drids- (4,5), dadurch gekennzeichnet, dass man einen 4-Methoxyphenylacetiminoäther mit lithylendiamin umsetzt. Das so gewonnene ?-(4'-3#letboxybenzy 1 )- imida.zol-dihydrid-(4,5) bildet farblose Kri stalle vom r. <B>118</B> bis 120'. Sein Hydrochlo- rid ist ein farbloses Kristallpulver. PATENTAN SPRUCI3 Process for the preparation of an imidazoldihydrids- (4,5) substituted in the 2 position, characterized in that a 4-methoxyphenylacetiminoether is reacted with lithylenediamine. The? - (4'-3 # letboxybenzy 1) - imida.zol-dihydrid- (4,5) obtained in this way forms colorless crystals of the r. <B> 118 </B> to 120 '. Its hydrochloride is a colorless crystal powder. Die neue Verbindung kann als Arznei mittel verwendet werden. UNTERANSPRtrCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung 4-i4Tethoxyphenylacetiminoäthylä,ther ver wendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Unisetzung einen 4-blethox5-phenylacetiminoäther ver wendet., der aus einem Salz desselben er halten wurde. 3. The new compound can be used as a medicine. SUB-CLAIM 1. Process according to claim, characterized in that 4-i4-thoxyphenylacetiminoethyl ether is used for the reaction. 2. The method according to claim, characterized in that a 4-blethox5-phenylacetiminoether is used for unisposition. Which was obtained from a salt thereof. 3. Verfahren nach Patentanspruch und Un teranspruch 2, dadurch gekennzeichnet, dass man zur Umsetzung einen 4-IVle- tliox3r-plienvlaeetiiuinoäther verwendet" der ans einem Hydrohalogenid desselben er halten wurde. 4. Verfahren nach Patentanspruch und den Unteranspriichen \3 und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 4-lletlioxyplienvlacetiminoäther ver- -endet, der aus dem Hydroohlorid dessel ben erhalten wurde. 5. Process according to patent claim and sub-claim 2, characterized in that a 4-IVle- tliox3r-plienvlaeetiiuinoether is used for the reaction "which was obtained from a hydrohalide of the same. 4. Process according to patent claim and dependent claims 3 and 3, characterized that a 4-lletlioxyplienvlacetiminoether obtained from the hydrochloride of the same is used for the reaction. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung 4-31e- l,liox-,>plienylacetiminaätliy läther verwen det, der aus dem Hydrochlorid desselben erhalten wurde. Process according to patent claim and the dependent claims 1 to 4, characterized in that for the reaction 4-31e- l, liox -,> plienylacetiminaätliy läther used which was obtained from the hydrochloride thereof.
CH204727D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204727A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204727T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204727A true CH204727A (en) 1939-05-15

Family

ID=25723380

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204727D CH204727A (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) CH204727A (en)

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