CH204738A - 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
CH204738A
CH204738A CH204738DA CH204738A CH 204738 A CH204738 A CH 204738A CH 204738D A CH204738D A CH 204738DA CH 204738 A CH204738 A CH 204738A
Authority
CH
Switzerland
Prior art keywords
naphthyl
dihydride
methoxy
imidazole
ether
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 CH204738A publication Critical patent/CH204738A/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,ü).       Gegenstand des vorliegenden     Patentes    ist  eine Verfahren zur Darstellung     eines    in       2-Stellung    substituierten     Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     2-Methoxy-naphthyl-(1)-acet-          iminoäther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-[2'-Methoxy-naph-          thyl-(1')-methyl]-imidazol-dihydrid-(4,5)    bil  det farblose Kristalle vom F. 147 bis 148'.  Sein Hydrochlorid ist ein farbloses Kristall  pulver.  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  2,9 Teile     2-Methoxy-naphthyl-(1)-acet-          iminoäthyläther-hydrochlorid    der Formel  
EMI0001.0016     
    (hergestellt aus     2-Methoxy-naphthyl-        (1)-          acetonitril),    aus dem sich während der Um  setzung     2-Methoxy-naphthyl-(1)-acetimino-          äthyläther    bildet, werden     in    15 Teilen abso  lutem 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 Alkohol, versetzt den Rückstand       mit    verdünnter Natronlauge und extrahiert       erschöpfend    mit Benzol. Nach dem Trocknen  über Pottasche wird das     2-[2'-Methoxy-naph-          thyl-(1')-methyl]-imidazol-dihydrid-(4,5)    der  Formel  
EMI0001.0030     
    aus     Toluol    umkristallisiert.  



  An Stelle von     2-Methoxy-naphthyl-(1)-          acetiminoäthyläther    kann     ebensogut    ein an-      derer Äther, wie z. B. der     Methyl-,        Propyl-          oder        Butyläther    Verwendung finden.  



  Statt vom salzsauren Salz des     2-Me-          thoxy-naphthyl-(1)-acetiininoä.thers    kann man  auch von einem andern Salze, wie z. B. vom       bromwasserstoffsauren,    vom schwefelsauren  oder vom     methylschwefelsauren    Salz aus  gehen.



  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 2-methoxy-naphthyl- (1) -acetiminoether is reacted with ethylenediamine.



  The 2- [2'-methoxy-naphthyl- (1 ') -methyl] -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals with a melting point of 147 to 148'. Its hydrochloride is a colorless crystal powder.



  The new compound can be used as a medicine.



  <I> Example: </I> 2.9 parts of 2-methoxy-naphthyl- (1) -acet- iminoethyl ether hydrochloride of the formula
EMI0001.0016
    (made from 2-methoxy-naphthyl- (1) - acetonitrile), from which 2-methoxy-naphthyl- (1) -acetimino-ethyl ether is formed during the implementation, 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 extracted exhaustively with benzene. After drying over potash, the 2- [2'-methoxy-naphthyl- (1 ') -methyl] -imidazole-dihydride- (4,5) of the formula
EMI0001.0030
    recrystallized from toluene.



  Instead of 2-methoxy-naphthyl- (1) -acetiminoethyl ether, another ether, such as e.g. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 2-methoxy-naphthyl- (1) -acetiininoä.thers one can also use another salt, such as. B. from the hydrobromic acid, from the sulfuric acid or from the methylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in 2-Stel- lung substituierten Iniidazoldihydrids-(4,5), dadurch gekennzeichnet, dass man einen ?- Methoxy-naphthyl-(1)-acetiminoäther mit Äthylendiamin umsetzt. Das so gewonnene 2-['?'-TAlethoxy-naph- thyl.(1')-methyl]-imidazol-dihydrid-(4,5) bil det farblose Kristalle vom F. 147 bis 148 . Sein Hydrochlorid ist ein farbloses Kristall pulver. Die neue Verbindung kann als Arznei mittel verwendet werden. PATENT CLAIM: Process for the preparation of an iniidazole dihydride (4,5) substituted in 2-position, characterized in that a? - methoxy-naphthyl- (1) -acetiminoether is reacted with ethylenediamine. The 2 - ['?' - T-alethoxy-naphthyl. (1 ') - methyl] -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals with a melting point of 147 to 148. Its hydrochloride is a colorless crystal powder. The new compound can be used as a medicine. UN TERAN SPRtrCHE 1. Verfahren nach Pa.tenta.nspruch, dadurch gekennzeichnet, dass man zur Unisetzung - Methoxy - naphthyl - (1) - acetiminoäthyl- < ither verwendet. ?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen 2 -31ethoxy-naphthyl-(1)-acetimino- äther verwendet, der aus einem Salz des selben erhalten wurde. 3. UN TERAN LANGUAGE 1. Method according to Pa.tenta.nspruch, characterized in that methoxy - naphthyl - (1) - acetiminoethyl - <ither is used for unisposition. ?. Process according to patent claim, characterized in that a 2 -31ethoxy-naphthyl- (1) -acetimino ether is used for the reaction, which was obtained from a salt of the same. 3. Verfahren nach Patentanspruch und Un- tera.nsprucli 2, dadurch gekennzeichnet, dass man zur Unisetzung einen ?-i@lethoxy- naphthyl - (1) - acetiininoäilier verwendet, der aus einem Hydrohalogenid desselben erhalten wurde. 4. Process according to patent claim and sub-claim 2, characterized in that a? -I @ lethoxy-naphthyl - (1) - acetiininoäilier which was obtained from a hydrohalide of the same is used for the reaction. 4th Verfahren nach Patentanspruch und den Unteransprüchen 2 und 3, dadurch ge kennzeichnet, dass inan zur Umsetzung einen 2-31ethoxy-naphthyl-(1)-acetimino- äther verwendet, der aus dem Hydrochlo- rid desselben erhalten wurde. 5. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet, da,ss nian zur Umsetzung 2- 331ethoxy-naphthyl-(:1)-acetiminoäthyläther verwendet, der aus dem Hydrochlorid des selben erhalten wurde. Process according to patent claim and dependent claims 2 and 3, characterized in that a 2-31ethoxy-naphthyl- (1) -acetimino ether is used for the reaction, which was obtained from the hydrochloride of the same. 5. The method according to claim and the dependent claims 1 to 4, characterized in that ss nian for the implementation of 2- 331ethoxy-naphthyl - (: 1) -acetiminoethyl ether is used, which was obtained from the hydrochloride of the same.
CH204738D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204738A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204738T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204738A true CH204738A (en) 1939-05-15

Family

ID=25723391

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204738D CH204738A (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) CH204738A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410562B1 (en) 1998-12-18 2002-06-25 Eli Lilly And Company Hypoglycemic imidazoline compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6410562B1 (en) 1998-12-18 2002-06-25 Eli Lilly And Company Hypoglycemic imidazoline compounds

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