[go: up one dir, main page]

CH204728A - 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
CH204728A
CH204728A CH204728DA CH204728A CH 204728 A CH204728 A CH 204728A CH 204728D A CH204728D A CH 204728DA CH 204728 A CH204728 A CH 204728A
Authority
CH
Switzerland
Prior art keywords
imidazole
dihydride
reaction
substituted
preparation
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 CH204728A publication Critical patent/CH204728A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     Imidazoldibydrids-(4,6).       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     3,4-Dimethoxyphenylacet-          iminoäther    mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(3',4'-Dimethoxyben-          zyl)-imidazol-dihydrid-(4,5)    bildet farblose  Kristalle vom F. 88 bis<B>90'</B> und vom     Kpo,o4     154 bis 155  . Sein Hydrochlorid ist ein  farbloses Kristallpulver vom F. 210 bis 2110.  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>       3,4-Dimethoxyphenylacetiminoäthyläther-          hvdrochlorid    der Formel  
EMI0001.0014     
    (hergestellt aus 1,7 Teilen     3,4-Dimethoxy-          phenylacetonitril),    aus dem sich während der    Umsetzung     3,4-Dimethoxyphenylacetimino-          äthyläther    bildet, wird in 15 Teilen absolu  tem 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 bei  guter Eiskühlung mit Natronlauge und extra  hiert erschöpfend mit Benzol.

   Nach dem  Trocknen über Pottasche wird das     2-(3',4'-Di-          methoxybenzyl)-imidazoldihydrid-(4,5)    der  Formel  
EMI0001.0022     
    bei 0,04 mm destilliert.  



  An Stelle von     3,4-Dimethoxyphenylacet-          iminoäthyläther    kann ebensogut ein anderer  Äther, wie z. B. der     Methyl-,        Propyl-    oder       Butyläther    Verwendung finden.  



  Statt vom salzsauren Salz des     3,4-Di-          methoxyphenylacetiminoäthers    kann man      auch von einem andern Salze, wie z. B. vom       bromwasserstoffsauren,    vom schwefelsauren  oder vom     methylschwefelsauren    Salz     aus-          zehen.  



  Process for the preparation of a 2-substituted imidazole dibydride- (4,6). 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 3,4-dimethoxyphenylacetiminoether is reacted with ethylenediamine.



  The 2- (3 ', 4'-dimethoxybenzyl) -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals from F. 88 to <B> 90' </B> and from Kpo, o4 154 to 155. Its hydrochloride is a colorless crystal powder with a F. 210 to 2110.



  The new compound can be used as a medicine.



  <I> Example: </I> 3,4-Dimethoxyphenylacetiminoäthyläther- hydrochloride of the formula
EMI0001.0014
    (prepared from 1.7 parts of 3,4-dimethoxyphenylacetonitrile), from which 3,4-dimethoxyphenylacetiminoethyl ether is formed during the reaction, is 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 sodium hydroxide solution while cooling with ice and then exhaustively with benzene.

   After drying over potash, the 2- (3 ', 4'-dimethoxybenzyl) -imidazole dihydride (4,5) of the formula
EMI0001.0022
    distilled at 0.04 mm.



  Instead of 3,4-Dimethoxyphenylacet- iminoäthyläther, another ether, such as z. B. the methyl, propyl or butyl ethers are used.



  Instead of the hydrochloric acid salt of 3,4-dimethoxyphenylacetiminoether one can also use another salt, such as. For example, avoid the hydrobromic acid, the sulfuric acid or the methylsulfuric acid salt.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines in 2- Stellung substituierten Imidazoldihydrids- (4,5), dadurch gekennzeichnet, dass man einen 3,4 - Dimethoxyphenylacetiminoit;lier mit Äthylendiamin umsetzt. Das so gewonnene 2-(3',4'-Dimetlioxvben- zyl)-imidazol-dihydrid-(4,5) bildet farblose Kristalle vom F. 88 bis 90 und vom Kp",", 154 bis<B>1.55</B> . Sein Hydrochlorid ist ein farbloses Kristallpulver vom F. 221<B>0</B> bis 21<B>1.</B> . Claim: A process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, characterized in that a 3,4-dimethoxyphenylacetiminoit; lier is reacted with ethylenediamine. The 2- (3 ', 4'-Dimetlioxvben- zyl) -imidazole-dihydride- (4,5) obtained in this way forms colorless crystals from F. 88 to 90 and from bp ",", 154 to <B> 1.55 </ B>. Its hydrochloride is a colorless crystal powder from F. 221 <B> 0 </B> to 21 <B> 1. </B>. Die neue Verbindung kann als Arznei mittel verwendet werden. UN TERAN SPRMHE 1. Verfahren nach Patenta.nsprueh, dadurch gekennzeichnet, dass man zur Umsetzung 3.4 - Dimethoxypheny lacetimirioäthvlätli(-r verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen 3,4-1)iniethoxyphenylacetiminoäther verwendet, der aus einem Salz desselben erhalten wurde. 3. The new compound can be used as a medicine. UN TERAN SPRMHE 1. Method according to Patenta.nsprueh, characterized in that one uses 3.4 - Dimethoxypheny lacetimirioäthvlätli (-r. 2. Method according to patent claim, characterized in that one uses a 3.4-1) iniethoxyphenylacetiminoether for the reaction, obtained from a salt thereof. 3. Verfahren nach Patentanspruch und Un teranspruch 2, dadurch gekennzeichnet, (lass man zur Umsetzung einen 3,4-Di- rnetlioxyphenylacetirninoäther verwendet, der aus einem Hy drohalogenid desselben erhalten wurde. 4. Verfahren nach Patentanspruch und den Unteranspriichen 2 lind 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 3,4-Dimethoxyphenylacetiminoäther verwendet, der aus dem Hydrochlorid des selben erhalten wurde. 5. Process according to claim and sub-claim 2, characterized in that a 3,4-di-methyl-oxyphenylacetirninoether obtained from a hydrohalide thereof is used for the reaction. 4. Process according to claim and dependent claims 2 and 3, characterized that a 3,4-dimethoxyphenylacetiminoether is used for the reaction, which was obtained from the hydrochloride of the same. Verfahren nach Patentanspruch und den Unteranspriiehen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung 3,4-Di- ni.ethoxyphenylacetiminoäthyläther ver wendet, der aus dem Hydrochlorid dessel ben erbalten wurde. Process according to patent claim and sub-claims 1 to 4, characterized in that 3,4-Di- ni.ethoxyphenylacetiminoethyl ether, which was obtained from the hydrochloride thereof, is used for the reaction.
CH204728D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204728A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204728T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204728A true CH204728A (en) 1939-05-15

Family

ID=25723381

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204728D CH204728A (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) CH204728A (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

Similar Documents

Publication Publication Date Title
CH204728A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204742A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204740A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204739A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204729A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204725A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204745A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204737A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204736A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204738A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204727A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204747A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204734A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204732A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204741A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204746A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204726A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204743A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
CH204744A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
DE835141C (en) Process for the preparation of ª ‡ -Ketocarbonsaeurenitrilen
AT219599B (en) Process for the preparation of new, basic substituted thioethers of pyrimidines
CH204730A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.
DE539806C (en) Process for the preparation of isopropylallylbarbituric acid
AT150315B (en) Process for the preparation of salicylic acid [β-acyloxyethyl] esters.
CH199906A (en) Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position.