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CH204732A - 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
CH204732A
CH204732A CH204732DA CH204732A CH 204732 A CH204732 A CH 204732A CH 204732D A CH204732D A CH 204732DA CH 204732 A CH204732 A CH 204732A
Authority
CH
Switzerland
Prior art keywords
pyridine
dihydride
imidazole
reaction
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 CH204732A publication Critical patent/CH204732A/en

Links

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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine 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     ss-Pyridin-formiminoäther    mit       Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(ss-Pyridyl)-imidazol-          dihydrid-(4,5)    bildet farblose Kristalle vom  F. 104 bis<B>105'</B> und vom     Kps    172 bis<B>173'.</B>  Sein Hydrochlorid ist ein farbloses Kristall  pulver.  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



       Beispiel:          ss-Pyridin-f        ormiminoäthyläther-hydrochlo-          rid    der Formel  
EMI0001.0015     
    (hergestellt aus 1,2 Teilen     Nicotinsäurenitril),       aus dem sich     während    der Umsetzung     ss-Py-          ridin-formiminoäthyläther    bildet, wird in 30  Teilen absolutem Alkohol gelöst. Man fügt  ziemlich rasch 1 Teil     Äthylendiamin    hinzu,  erhitzt langsam auf 100   und hält einige  Stunden bei dieser Temperatur. Hernach ver  treibt man den Alkohol, versetzt den Rück  stand mit Natronlauge und extrahiert er  schöpfend mit Chloroform.

   Der Chloroform  rückstand wird aus     Toluol    umkristallisiert  und stellt     2-ss-Pyridylimidazoldihydrid-(4,5)     der Formel  
EMI0001.0023     
    dar.  An Stelle von     ss-Pyridin-formiminoäthyl-          äther    kann ebensogut ein anderer Äther, wie  z. B. der     Methyl-,        Propyl-    oder     Butyläther          Verwendung    finden.  



  Statt vom salzsauren Salz des     ss-Pyridin-          formimin.oäthers    kann man auch von einem           andern    Salze, wie z. B. vom     bromwasserstof        f-          sauren,    vom schwefelsauren oder vom nie  thylschwefelsauren 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 an β-pyridine formimino ether is reacted with ethylenediamine.



  The 2- (ss-pyridyl) -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals from F. 104 to <B> 105 '</B> and from Kps 172 to <B> 173'. </ B> Its hydrochloride is a colorless crystal powder.



  The new compound can be used as a medicine.



       Example: ss-pyridine formiminoethyl ether hydrochloride of the formula
EMI0001.0015
    (made from 1.2 parts of nicotinic acid nitrile), from which β-pyridine-formiminoethyl ether is formed during the reaction, is dissolved in 30 parts of absolute alcohol. One part of ethylenediamine is added fairly quickly, heated slowly to 100 and held at this temperature for a few hours. Then the alcohol is driven off, the residue is mixed with sodium hydroxide solution and extracted with chloroform.

   The chloroform residue is recrystallized from toluene and provides 2-ß-pyridylimidazole dihydride (4.5) of the formula
EMI0001.0023
    instead of ß-pyridine-formiminoäthyl- ether can just as well another ether, such as z. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of the ss-pyridine formimin.oether one can also use another salt, such as B. from the hydrobromic acid, the sulfuric acid or the never-thylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in 2 Stellung substituierten Imidazoldihydrids- (4,5), dadurch gekennzeichnet, dass man einen ss-Pyridin-formiminoäther mit. Athylendianiin umsetzt. Das so gewonnene 2-(ss-Pyridyl)-imidazol- dihydrid-(4,5) bildet farblose Kristalle vom F. 104 bis<B>105'</B> und vom Kp, <B>1722)</B> bis<B>1.73'.</B> Sein Hydrochlorid ist ein farbloses Kristall pulver. 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 one ss-pyridine-formiminoether with. Ethylendianiin converts. The 2- (ss-pyridyl) -imidazole- dihydride- (4,5) obtained in this way forms colorless crystals from F. 104 to <B> 105 '</B> and of bp, <B> 1722) </B> up to <B> 1.73 '. </B> Its hydrochloride is a colorless crystal powder. The new compound can be used as a medicine. SUBCLAIMS 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung ss-Pyridin-formiminoäthyläther verwendet. \?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen ss-Pyi@idin-formiminoätlier verwen det, der aus einem Salz desselben erhalten wurde. 3. Verfahren nach Patentanspruch und Un teranspruch ?, dadurch gekennzeichnet, dass man zur Umsetzung einen ss-Pyridin- foriniminoätlier verwendet, der aus einem Hydrolialogenid desselben erhalten wurde. 4. Process according to patent claim, characterized in that β-pyridine-formiminoethyl ether is used for the reaction. \ ?. Process according to claim, characterized in that an ss-Pyi @ idin-formiminoätlier is used for the reaction, which was obtained from a salt thereof. 3. The method according to claim and sub-claim?, Characterized in that an s-pyridine foriniminoätlier is used for the implementation, which was obtained from a hydrolialogenide thereof. 4th Verfahren nach Patentanspruch und den Unteransprüchen ? und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen ss-Pyridin-foi-niiminoäther verwen det, der aus dein Hydrochlorid desselben erhalten wurde. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung ss-Pyri- din-formiminoäthylä ther verwendet, der aus dem Hydrochlorid desselben erhalten wurde. Method according to patent claim and the subclaims? and 3, characterized in that an β-pyridine-foi-niiminoether, which was obtained from the hydrochloride of the same, is used for the reaction. Process according to patent claim and the dependent claims 1 to 4, characterized in that β-pyridine-formiminoethyl ether obtained from the hydrochloride of the same is used for the reaction.
CH204732D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204732A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204732T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204732A true CH204732A (en) 1939-05-15

Family

ID=25723385

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204732D CH204732A (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) CH204732A (en)

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