CH204740A - 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
CH204740A
CH204740A CH204740DA CH204740A CH 204740 A CH204740 A CH 204740A CH 204740D A CH204740D A CH 204740DA CH 204740 A CH204740 A CH 204740A
Authority
CH
Switzerland
Prior art keywords
quinoline
imidazole
dihydride
process according
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 CH204740A publication Critical patent/CH204740A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon 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,ü).       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     Chinolin-(8)-acetiminoäther     mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-[Chinolin-(8')-me-          thyl]-imidazol-dihydrid-(4,5)    bildet farblose  Kristalle vom F. 98 bis<B>95'</B> und vom KP""  190 bis 192  .     Sein        Dihydrochlorid    ist ein  farbloses Kristallpulver vom Zersetzungs  punkt 260 bis 261  .  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



       Beispiel:     2,1 Teile     Chinolin-(8)-acetiminoäthyl-          äther-dihydrochlorid    der Formel  
EMI0001.0015     
    (hergestellt aus     Chinolin-(8)-acetonitril),    aus  dem sich während der Umsetzung     Chinolin-          (8)-acetiminoäthyläther    bildet, werden in 15  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 ver  treibt man den Alkohol, versetzt den Rück  stand mit verdünnter Natronlauge     und    extra  hiert erschöpfend mit Benzol. Nach dem  Trocknen über Pottasche wird das 2-     [Chi-          nolin-    (8')     -methyll        -imidazol-dihydrid-    (4,5)  der Formel  
EMI0001.0028     
    bei 0,05 mm destilliert.  



  An Stelle von     Chinolin-(8)-acetimino-          äthyläther        kann    ebensogut ein anderer Äther,  wie z. B. der     Methyl-,        Propyl-    oder     Butyl-          äther    Verwendung finden.      Statt vom salzsauren Salz des     Chinolin-          (8)-acetiminoä.thers    kann man auch von  einem andern Salze, wie z. B. vom     brom-          wa,sserstoffsauren,    vom schwefelsauren oder  vom     methylschwefelsauren    Salz ausgehen.



  Process for the preparation of an imidazole dihydride (4, u) 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 quinoline (8) acetimino ether is reacted with ethylenediamine.



  The 2- [quinoline- (8 ') -methyl] -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals from F. 98 to <B> 95' </B> and from KP "" 190 to 192. Its dihydrochloride is a colorless crystal powder with a decomposition point of 260 to 261.



  The new compound can be used as a medicine.



       Example: 2.1 parts of quinoline (8) acetiminoethyl ether dihydrochloride of the formula
EMI0001.0015
    (made from quinoline (8) acetonitrile), from which quinoline (8) acetiminoethyl ether is formed during the reaction, are dissolved in 15 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 driven off, the residue is mixed with dilute sodium hydroxide solution and an extra amount of benzene is added. After drying over potash, the 2- [quinoline- (8 ') -methyll -imidazole-dihydride- (4,5) of the formula
EMI0001.0028
    distilled at 0.05 mm.



  Instead of quinoline- (8) -acetimino- äthyläther, another ether, such as z. B. the methyl, propyl or butyl ethers are used. Instead of the hydrochloric acid salt of the quinoline- (8) -acetiminoä.thers one can also use another salt, such as B. from the bromine, hydrogen acid, sulfuric acid or methylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in 2-Stellung substituierten Imidazoldihydrids- (.1,5), dadurch gekennzeichnet, dass inan einen Chinolin-(8)-acetiininoäther mit Äthy- lendiamin umsetzt. PATENT CLAIM: Process for the preparation of an imidazole dihydride (.1,5) substituted in the 2-position, characterized in that a quinoline (8) -acetiininoether reacts with ethylenediamine. Das so gewonnene ?-[Chinolin-(8')-nie- thyl]-imidazol-dibydrid-(.1,5) bildet farblose Kristalle vom F. 93 bis 95 und vom KpO", 0 bis<B>192'.</B> Sein Dihy drochlorid ist ein farLloses Kristallpulver vom Zersetzungs punkt 260 bis 261 0. Die neue Verbindung kann als Arznei mittel verwendet werden. TJNTERANSPRü CHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung Chinolin-(8)-acetiminoäthyläther verwen det. ?. The? - [quinoline- (8 ') - methyl] -imidazole-dibydride - (. 1,5) obtained in this way forms colorless crystals from F. 93 to 95 and from KpO ", 0 to <B> 192'. </B> Its dihydrochloride is a colorless crystal powder with a decomposition point of 260 to 261 0. The new compound can be used as a medicament. TJNTERANSPRü CHE 1. Process according to patent claim, characterized in that quinoline (8) - acetiminoethyl ether used.?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen (,iiinolin-(8)-acetiminoäther verwen det, der ans einem Salz desselben erhal ten wurde. 3. Verfahren nach Patentanspruch und Un teranspruch -?, dadurch gekennzeichnet, dass man zur Umsetzung einen Chinolin- (8)-acetiininoäther verwendet, der aus einem Hydrohalogenid desselben erhalten Wurde. d. A process according to claim, characterized in that a (, iiinolin- (8) -acetiminoether which was obtained from a salt thereof is used for the reaction. 3. Process according to claim and sub-claim - ?, characterized in that one is used for Implementation of a quinoline (8) acetiinino ether obtained from a hydrohalide of the same d. Verfahren nach Patentanspruch und den U nteranspriichen ? und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen Chinolin-(8 )-acetiminoäther verwen det, der ans dein Dihydrochlorid desselben erhalten wurde. . Verfahren nach Patentanspruch und den Unteraiispriiehen 1. bis :1, dadurch gekenn zeichnet, dass man zur Umsetzung Chino- lin-(8)-acetiminoäthvläther verwendet, der aus dein Dihvdroelilorid desselben erhal ten wurde. Procedure according to the patent claim and the subclaims? and 3, characterized in that a quinoline- (8) -acetiminoether is used for the reaction, which was obtained from the dihydrochloride of the same. . Process according to claim and sub-sections 1. to: 1, characterized in that quinoline- (8) -acetiminoäthvläther is used for the implementation, which was obtained from the dihvdroeliloride thereof.
CH204740D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204740A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204740T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204740A true CH204740A (en) 1939-05-15

Family

ID=25723393

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204740D CH204740A (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) CH204740A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2433525A1 (en) * 1978-08-15 1980-03-14 Pfizer NOVEL IMIDAZOLE DERIVATIVES, THEIR PRODUCTION PROCESS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2433525A1 (en) * 1978-08-15 1980-03-14 Pfizer NOVEL IMIDAZOLE DERIVATIVES, THEIR PRODUCTION PROCESS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM

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