CH204725A - 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
CH204725A
CH204725A CH204725DA CH204725A CH 204725 A CH204725 A CH 204725A CH 204725D A CH204725D A CH 204725DA CH 204725 A CH204725 A CH 204725A
Authority
CH
Switzerland
Prior art keywords
sep
same
ether
reaction
process according
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 CH204725A publication Critical patent/CH204725A/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

  

  
EMI0001.0001     
  
    Verfahren <SEP> zur <SEP> Darstellung <SEP> eines <SEP> in <SEP> 2-Stellung <SEP> sabstitnierten <SEP> Imidazoldihydrids-(4,5).            Gegenstand    des vorliegenden     Patentes    ist  ein Verfahren zur     Darstellung        eines    in     2-          Stellung    substituierten     Imidazoldihydrids-          (4,5),        welches    :dadurch     gekennzeichnet    ist;  .dass man einen     2.,3,4-Trimethoxyphenylacet-          iminoäther    mit     Äthylendiamn    umsetzt.  



  Das so gewonnene 2-(2',3',4'     Trimethoxy-          benzyl)    -     imidazoldihydrid    - (4,5) bildet     farb-          lose        Kristalle    vom F. 86     bis   <B>87'.</B>     Sein        Ilydro-          ±hlorid        ist    ein farbloses     Kristallpulver.     



  Die neue     Verbindung    kann     als    Arznei  mittel verwendet werden.  



       Beispiel:     3 Teile     2,3,4-Trimethoxyphenyl-a@cetimino-          äthyläther-hydrochlorid    ,der Formel  
EMI0001.0032     
         (hergestellt    aus     2,3a4    -     Trimethoxy    - phenyl-         acetonitril),    aus dem sich während der Um  -etzung     2,3,4-Trimethoxy-phenyl-acetimino-          äthyläther    bildet, werden in 15 Teilen ab  solutem 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          rsc   <B>1</B> mit Benzol.

   Nachdem     Trocknen     e     'höpfenc     über     Pottasche        wird        das        '2-(2',3',4'-Trimeth-          oxybenzyl)-imidazoldihydrid-@(4;5)    der For  mel .  
EMI0001.0054     
  
EMI0001.0055     
  
    bei <SEP> 0,15 <SEP> mm <SEP> destilliert.
<tb>  



  An <SEP> :Stelle <SEP> von <SEP> 2,3;4-Trimethoxyphenyl  acetiminoäthyläther <SEP> kann. <SEP> ebensogut <SEP> ein <SEP> an  derer <SEP> Äther, <SEP> wie <SEP> z. <SEP> B. <SEP> der <SEP> Methyl-, <SEP> Propyl  oder <SEP> Butyläther, <SEP> Verwendung <SEP> finden.              Statt    vom salzsauren Salz des     Trimeth-          oxyphenylacetiminoäthers    kann man     auch     von einem     andern    Salze, wie z. B. vom     brom-          wasserstoffsauren,    vom     sch-tvefelsaureii    oder  vom     methylschwefelsa.uren    Salz ausgehen.



  
EMI0001.0001
  
    Method <SEP> for <SEP> representation <SEP> of a <SEP> in <SEP> 2-position <SEP> sabstituted <SEP> imidazole dihydride- (4,5). The present patent relates to a process for the preparation of a 2-position substituted imidazole dihydride (4,5), which is characterized by; .that one reacts a 2., 3,4-trimethoxyphenylacet- iminoether with ethylenediamine.



  The 2- (2 ', 3', 4 'trimethoxybenzyl) - imidazole dihydride - (4,5) obtained in this way forms colorless crystals from F. 86 to <B> 87'. </B> Its Ilydro- ± Chloride is a colorless crystal powder.



  The new compound can be used as a medicine.



       Example: 3 parts of 2,3,4-trimethoxyphenyl-a @ cetimino ethyl ether hydrochloride, of the formula
EMI0001.0032
         (made from 2,3a4 - trimethoxy - phenyl acetonitrile), from which 2,3,4-trimethoxy-phenyl-acetimino-ethyl 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 extracted rsc <B> 1 </B> with benzene.

   After drying e 'höpfenc over potash, the' 2- (2 ', 3', 4'-trimethoxybenzyl) imidazole dihydride - @ (4; 5) of the formula.
EMI0001.0054
  
EMI0001.0055
  
    at <SEP> 0.15 <SEP> mm <SEP> distilled.
<tb>



  At <SEP>: place <SEP> of <SEP> 2,3; 4-trimethoxyphenyl acetiminoethyl ether <SEP> can. <SEP> just as well <SEP> one <SEP> on which <SEP> ether, <SEP> as <SEP> z. <SEP> B. <SEP> the <SEP> methyl, <SEP> propyl or <SEP> butyl ether, <SEP> use <SEP>. Instead of the hydrochloric acid salt of Trimeth- oxyphenylacetiminoäthers you can also use another salt, such as. B. from the hydrobromic acid, the sch-tvefelsaureii or the methylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in ? Stellung substituierten Imidazoldihy drids- (4,5), dadurch gekennzeichnet, dass man einen 2,3,4 - Trimethoxyphenylacetiminoäther mit 9.thylendiamin umsetzt. PATENT CLAIM: Method for the representation of an in? Position substituted imidazoldihy drids- (4,5), characterized in that a 2,3,4 - trimethoxyphenylacetiminoether is reacted with 9.thylenediamine. Das so gewonnene 2-(2',3',4'-Trimethoxy- benzyl) - imidazol.diliytlricl - (4,5) bildet farb lose Kristalle vom F. 86 bis <B>87'.</B> Sein Hydro- chlorid ist ein farbloses Kristallpulver. Die neue Verbindung kann als Arznei mittel verwendet werden. UN TERANTSPRMIE 1. The 2- (2 ', 3', 4'-trimethoxybenzyl) - imidazol.diliytlricl - (4,5) obtained in this way forms colorless crystals from F. 86 to <B> 87 '. </B> Its hydro - chloride is a colorless crystal powder. The new compound can be used as a medicine. UN TERANT PREMIUM 1. Verfahren nach Patentanspruch, -dadurch gekennzeichnet, dass man zur Umsetzung 2,3,4 - Trimethoxyphenylacetiminoäthyl- äther verwendet. ?. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen 2,8,-1- - Triinetlioxyphenylacetimino- äther verwendet, der aus einem Salz des selben erbalten wurde. Process according to claim, characterized in that 2,3,4 - trimethoxyphenylacetiminoethyl ether is used for the reaction. ?. Process according to patent claim, characterized in that a 2,8, -1- - Triinetlioxyphenylacetimino- ether is used, which was obtained from a salt of the same. V erfi -ihreii ii- ach Patc -ntaiispri-tüli und Un- teranspru, i 9., dadureh gekennzeichnet, dass man zur -Umsetzung einen 2,3,4-Tri- inethoxyplienylacetiminoäther verwendet, der aus einem Hydrohalogenid desselben erhalten wurde. V erfi -ihreii ii- ach Patc -ntaiispri-tüli and Unter- teranspru, i 9., characterized in that a 2,3,4-tri- inethoxyplienylacetiminoether obtained from a hydrohalide of the same is used for the conversion. -1. Verfahren nach Patentanspruch und den Unteransprüchen 2 und 3, dadurch ge kennzeichnet. dass man zur Umsetzung einen 2,3,4 - Trimethoxyphenylacetimino- ätlier verwendet, der aus dem Hydro chlorid desselben erhalten wurde. 5. -1. Method according to patent claim and the dependent claims 2 and 3, characterized in that. that a 2,3,4-trimethoxyphenylacetimino ätlier is used for the reaction, which was obtained from the hydrochloride of the same. 5. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch ge kennzeichnet, dass man zur Umsetzung 2 , 3 , 4 - Tri metlioxyphenylacetiminoäthyl- äther verwendet, der aus dem Ilydro- chlori.d desselben erhalten wurde. Process according to claim and the dependent claims 1 to 4, characterized in that 2, 3, 4-tri-metlioxyphenylacetiminoethyl ether obtained from the Ilydro- chlori.d of the same is used for the reaction.
CH204725D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204725A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204725T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204725A true CH204725A (en) 1939-05-15

Family

ID=25723378

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Application Number Title Priority Date Filing Date
CH204725D CH204725A (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) CH204725A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3354175A (en) * 1962-04-12 1967-11-21 Merck Ag E 2-(2', 5'-dialkoxybenzyl)-2-imidazolines and related compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3354175A (en) * 1962-04-12 1967-11-21 Merck Ag E 2-(2', 5'-dialkoxybenzyl)-2-imidazolines and related compounds

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