CH204737A - 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
CH204737A
CH204737A CH204737DA CH204737A CH 204737 A CH204737 A CH 204737A CH 204737D A CH204737D A CH 204737DA CH 204737 A CH204737 A CH 204737A
Authority
CH
Switzerland
Prior art keywords
sep
naphthyl
dihydride
imidazole
man
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 CH204737A publication Critical patent/CH204737A/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

Description

  

  Verfahren zur Darstellung eines in     2-Stellung        substituierten        Imida.zordihydrids-(4,1i).       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung eines in       2-Stellung    substituierten     Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     Naphthyl-(1)-acetiminoäther     mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-[Naphthyl-(1')-me-          thyl]-imidazol-dihydrid-(4,5)    bildet farblose  Kristalle vom F. 119 bis 120'. Sein     Hydro-          chlorid    ist ein farbloses Kristallpulver vom  F. 252 bis 253  .  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  3 Teile     iNaphth5#1-(1)-acetiminoäthyläther-          hydrochlorid    der Formel  
EMI0001.0015     
    (hergestellt aus     Naphthyl-(1)-acetonitril),    aus         denn    sich während der Umsetzung     Naphthyl.          (1)-acetiminoäthyläther    bildet, werden in 15  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 verdünnter Natronlauge und extra  hiert erschöpfend mit Benzol.

   Nach dem  Trocknen über Pottasche wird das     2-[Naph-          thyl-(1')-methyl]-imidazol-dihydrid-(4,5)    der  Formel  
EMI0001.0023     
    aus Äther umkristallisiert.  



  An Stelle von     Naphthyl-(1)-acetimino-          äthyläther    kann ebensogut     ein        ander    Äther,  wie z. B. der     Methyl-,        Propyl-    oder     Butyl-          äther        Verwendung    finden,      Statt vom salzsauren Salz des     Na.plithyl-          (1)-acetiminoäthers    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 Imida.zordihydrids- (4,1i) substituted in the 2-position. 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 naphthyl (1) acetimino ether is reacted with ethylenediamine.



  The 2- [naphthyl- (1 ') -methyl] -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals with a melting point of 119 to 120'. Its hydrochloride is a colorless crystal powder from F. 252 to 253.



  The new compound can be used as a medicine.



  <I> Example: </I> 3 parts of iNaphth5 # 1- (1) -acetiminoethyl ether hydrochloride of the formula
EMI0001.0015
    (made from naphthyl- (1) -acetonitrile), because naphthyl. (1) Acetiminoäthyläther is dissolved in 15 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. The alcohol is then driven off, the residue is mixed with dilute sodium hydroxide solution and then exhaustively with benzene.

   After drying over potash, the 2- [naphthyl- (1 ') -methyl] -imidazole-dihydride- (4,5) of the formula
EMI0001.0023
    recrystallized from ether.



  Instead of naphthyl- (1) -acetimino- äthyläther can just as well another ether, such as. B. the methyl, propyl or butyl ether use, instead of the hydrochloric acid salt of Na.plithyl- (1) -acetiminoäthers you can also use another salt, such as. B. start with the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims (1)

EMI0002.0006 PATENTANSPRUCH.: <tb> Verfahren <SEP> zur <SEP> Darstellung <SEP> eines <SEP> in <SEP> 2-Stel lung <SEP> substituierten <SEP> Imidazoldihydrids-(4.,5), <tb> dadurch <SEP> gekennzeichnet, <SEP> dass <SEP> man <SEP> einen <tb> Naphthyl-(1)-acetiminoäthei- <SEP> mit <SEP> Xthylen diamin <SEP> umsetzt. <tb> Das <SEP> so <SEP> gewonnene <SEP> ?-@Na.piithyl-(1')-iiie tliyl]-imidazol-dihydrid-(d,5) <SEP> bildet <SEP> farblose <tb> Kristalle <SEP> vom <SEP> F. <SEP> <B>119</B> <SEP> bis <SEP> 120 <SEP> . <SEP> Sein <SEP> IIv <SEP> dro chlorid <SEP> ist <SEP> ein <SEP> farbloses <SEP> Kristalllnilver@ <SEP> vom <tb> F. <SEP> 252 <SEP> bis <SEP> 253 <SEP> . <tb> Die <SEP> neue <SEP> Verbindung <SEP> kann <SEP> als <SEP> Arznei mittel <SEP> verwendet <SEP> 'erden. <tb> UNTERANSPR <SEP> i7 <SEP> C<B>I</B>IE <tb> 1. EMI0002.0006 PATENT CLAIM: <tb> Method <SEP> for <SEP> representation <SEP> of a <SEP> in <SEP> 2-position <SEP> substituted <SEP> imidazole dihydride- (4th, 5), <tb> characterized by <SEP>, <SEP> that <SEP> man <SEP> a <tb> Naphthyl- (1) -acetiminoäthei- <SEP> with <SEP> Xthylenediamine <SEP>. <tb> The <SEP> obtained in this way <SEP>? - @ Na.piithyl- (1 ') - iiie tliyl] -imidazole-dihydride- (d, 5) <SEP> forms <SEP> colorless <tb> Crystals <SEP> from <SEP> F. <SEP> <B> 119 </B> <SEP> to <SEP> 120 <SEP>. <SEP> His <SEP> IIv <SEP> dro chloride <SEP> is <SEP> a <SEP> colorless <SEP> crystal silver @ <SEP> from <tb> F. <SEP> 252 <SEP> to <SEP> 253 <SEP>. <tb> The <SEP> new <SEP> connection <SEP> can <SEP> used as <SEP> medicinal product <SEP> <SEP> 'ground. <tb> SUB-CLAIM <SEP> i7 <SEP> C <B> I </B> IE <tb> 1. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> dadurch <tb> gekennzeichnet, <SEP> dass <SEP> man <SEP> zur <SEP> Umsetzung <tb> Naphthyl-(1)-acetiminoäthyläther <SEP> verwen det. EMI0002.0007 -'. <SEP> Verfahren <SEP> nach <SEP> Palentansprucli, <SEP> dadurch <tb> gekennzeielinet, <SEP> < lass <SEP> man <SEP> zur <SEP> Umsetzung <tb> einen <SEP> Naplitliyl-(1)-acetiininoäther <SEP> ver wendet, <SEP> der <SEP> ans <SEP> einem <SEP> Salz <SEP> desselben <SEP> er halten <SEP> Wurde. <tb> 3. <SEP> Verfahren <SEP> iia.eli <SEP> Patentanspruch <SEP> und <SEP> U <SEP> n teratispruc.h <SEP> 2, <SEP> (laeiiireli <SEP> gekennzeichnet, <tb> da.ss <SEP> man <SEP> zier <SEP> Umsetzung <SEP> einen <SEP> Naphthyl (1)-acetiminoäther <SEP> verwendet, <SEP> der <SEP> aus <tb> einem <SEP> Hydrohalogenid <SEP> desselben <SEP> erhalten <tb> wurde. <tb> 4. <SEP> method <SEP> according to <SEP> patent claim, <SEP> thereby <tb> marked, <SEP> that <SEP> man <SEP> for <SEP> implementation <tb> Naphthyl- (1) -acetiminoethylether <SEP> used. EMI0002.0007 - '. <SEP> procedure <SEP> according to <SEP> Palentansprucli, <SEP> thereby <tb> marked, <SEP> <let <SEP> man <SEP> for <SEP> implementation <tb> a <SEP> naplitliyl- (1) -acetiininoether <SEP> is used, <SEP> which has been <SEP> received <SEP> from <SEP> a <SEP> salt <SEP> of the same <SEP>. <tb> 3. <SEP> method <SEP> iia.eli <SEP> patent claim <SEP> and <SEP> U <SEP> n teratispruc.h <SEP> 2, <SEP> (laeiiireli <SEP> marked, <tb> da.ss <SEP> one <SEP> zier <SEP> implementation <SEP> a <SEP> naphthyl (1) -acetiminoether <SEP> is used, <SEP> the <SEP> from <tb> a <SEP> hydrohalide <SEP> of the same <SEP> obtained <tb> was. <tb> 4. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch <SEP> und <SEP> den <tb> 1'nleriiii:priiehen <SEP> ? <SEP> und <SEP> 3, <SEP> dadurch <SEP> ge kennzeichtiel, <SEP> dass <SEP> man <SEP> zur <SEP> Unisetzung <tb> einen <SEP> N;i <SEP> liiitliyl-(1)-acetiniinoäther <SEP> ver wendet, <SEP> der <SEP> aus <SEP> dein <SEP> 1.Iydrochlorid <SEP> dessel 1,en <SEP> erhalten <SEP> wurde. <tb> a. <SEP> Verfahren <SEP> nach <SEP> Patentanspruch <SEP> und <SEP> den <tb> Unteranspriiehen <SEP> l <SEP> his <SEP> 4, <SEP> dadurch <SEP> gekenn zeichnet, <SEP> dass <SEP> man <SEP> zur <SEP> Umsetzung <SEP> Naph thyl-(1)-acetiminoiit,liylätber <SEP> verwendet, <tb> der <SEP> aus <SEP> dem <SEP> Ilvclroelilorid <SEP> desselben <SEP> er halten <SEP> wurde. <SEP> method <SEP> according to <SEP> patent claim <SEP> and <SEP> den <tb> 1'nleriiii: priiehen <SEP>? <SEP> and <SEP> 3, <SEP> thereby <SEP> marked, <SEP> that <SEP> one <SEP> for <SEP> unisposition <tb> an <SEP> N; i <SEP> liiitliyl- (1) -acetiniinoether <SEP> is used, <SEP> the <SEP> from <SEP> your <SEP> 1st hydrochloride <SEP> of the 1, en <SEP> was received <SEP>. <tb> a. <SEP> method <SEP> according to <SEP> patent claim <SEP> and <SEP> den <tb> Subclaims <SEP> l <SEP> to <SEP> 4, <SEP> characterized by <SEP>, <SEP> that <SEP> man <SEP> for <SEP> implementation <SEP> Naphthyl- ( 1) -acetiminoiit, liylätber <SEP> used, <tb> the <SEP> from <SEP> the <SEP> Ilvclroelilorid <SEP> of the same <SEP> received <SEP>.
CH204737D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204737A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204737T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204737A true CH204737A (en) 1939-05-15

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ID=25723390

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204737D CH204737A (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) CH204737A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287469A (en) * 1963-09-27 1966-11-22 Du Pont Naphthyl-and indanylimidazolines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3287469A (en) * 1963-09-27 1966-11-22 Du Pont Naphthyl-and indanylimidazolines

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