CH204745A - 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
CH204745A
CH204745A CH204745DA CH204745A CH 204745 A CH204745 A CH 204745A CH 204745D A CH204745D A CH 204745DA CH 204745 A CH204745 A CH 204745A
Authority
CH
Switzerland
Prior art keywords
dihydride
imidazole
ether
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 CH204745A publication Critical patent/CH204745A/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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines in     2-Stellung    substituierten     Imidazoldihydrids-(4,5).       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     1-Naphtoxyacetiminoäther     mit     Äthylendiamin    umsetzt.  



  Das so gewonnene     2-(1'-Naphtoxymethyl)-          imidazol-dihydrid-(4,5)    bildet ein farbloses       Hydrochlorid    vom F. 235 bis 237  .  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  26,5 Teile     1-Naphtoxyacetiminoäthyl-          äther-hydrochlorid    der Formel  
EMI0001.0013     
    (hergestellt aus dem beim Erhitzen von     a-          Naphtol    mit     Chloracetonitril    in     Acetonlösung     und Gegenwart von Pottasche entstehenden         1-Naphtoxyacetonitril,        Kpo,r,    140 bis 143';  F. 65  ), aus dem sich während der Umset  zung     1-Naphtoxyacetiminoäthyläther    bildet,       werden    in absolutem Alkohol gelöst.

   Man  fügt ziemlich rasch 6 Teile     Äthylendiamin     hinzu, erhitzt langsam auf<B>100'</B> und hält  einige     Stunden    bei dieser Temperatur. Her  nach vertreibt man den Alkohol, versetzt den  Rückstand mit Natronlauge und extrahiert  erschöpfend mit Benzol. Nach dem     Trocknen     über Pottasche und     nachherigem    Vertreiben  des Benzols bleibt das     2-(1'-Naphtoxy-          methyl)-imidazoldihydrid-(4,5)    der Formel  
EMI0001.0028     
    zurück.  An Stelle von     1-Naphtoxyacetiminoäthyl-          äther    kann ebensogut ein anderer Äther, wie  z.

   B. der     Methyl-,        Propyl-    oder     Butyläther     Verwendung finden.           Statt    vom salzsauren Salz des     1-Na.pht-          oayacetiminoäthers    kann man auch von  einem andern Salze, wie z. B. vom     brom-          wa.sserstoffsauren,    vom schwefelsauren oder  vom     methylschwefelsauren    Salz ausgehen.



  Process for the preparation of an imidazole dihydride (4,5) 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 1-naphthoxyacetimino ether is reacted with ethylenediamine.



  The 2- (1'-naphtoxymethyl) - imidazole-dihydride- (4,5) obtained in this way forms a colorless hydrochloride with a melting point of 235 to 237.



  The new compound can be used as a medicine.



  <I> Example: </I> 26.5 parts of 1-naphtoxyacetiminoethyl ether hydrochloride of the formula
EMI0001.0013
    (made from the 1-naphtoxyacetonitrile, Kpo, r, 140 to 143 '; F. 65) which is formed when a-naphthol is heated with chloroacetonitrile in acetone solution and the presence of potash, from which 1-naphtoxyacetiminoethyl ether is formed during the reaction dissolved in absolute alcohol.

   6 parts of ethylenediamine are 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 and extracted exhaustively with benzene. After drying over potash and then driving off the benzene, the 2- (1'-naphthoxymethyl) imidazole dihydride (4,5) of the formula remains
EMI0001.0028
    back. Instead of 1-Naphtoxyacetiminoäthyl- ether, another ether, such as z.

   B. the methyl, propyl or butyl ethers are used. Instead of the hydrochloric acid salt of 1-Na.pht- oayacetiminoäthers one can also use another salt, such as z. B. from 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 1-Naphtoyyacetiminoäther mit Äthylen diamin umsetzt. Das so gewonnene 2-(1'-Naphtovvmetlivl)- imidazoldihydrid-(,4,5) bildet ein farbloses Hydrochlorid vom I'. 235 bis<B>237</B> . Die neue Verbindung kann als Arznei mittel verwendet werden. UNTERAN SPRCCHE 1. Claim: Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, characterized in that a 1-naphthoyyacetimino ether is reacted with ethylene diamine. The 2- (1'-Naphtovvmetlivl) - imidazole dihydride - (, 4,5) obtained in this way forms a colorless hydrochloride of I '. 235 to <B> 237 </B>. The new compound can be used as a medicine. SUB-LANGUAGE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung 1-Naphtogyacetiminoäthylätherverwendet. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen 1-Naphtoayacetiniinoäther verwen det, der aus einem Salz desselben erhalten wurde. 3. Process according to patent claim, characterized in that 1-naphthogyacetiminoethyl ether is used for the reaction. Process according to claim, characterized in that a 1-Naphtoayacetiniinoäther is used for the reaction, which was obtained from a salt thereof. 3. Verfahren nach Patentanspruch und I-n- teranspruch \?, dadurch gekennzeichnet, dass man zur Umsetzung einen 1-Napht- oxy acetimiiioäther verwendet, der aus einem H5 drolialogenid desselben erhalten wurde. 4. Verfahren nach Patentanspruch und den Unteranspriichen - und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen 1-Naplitoxyacetiminoäther verwen det, der aus dem Hydrochlorid desselben erhalten wurde. Process according to patent claim and first claim, characterized in that a 1-naphthoxyacetymium ether is used for the reaction, which was obtained from a hydrogen halide of the same. 4. The method according to claim and the dependent claims - and 3, characterized in that a 1-naplitoxyacetiminoether is used for the implementation, which was obtained from the hydrochloride of the same. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet, dass man zur Umsetzung 1- Naphtogy acetiminoäthyläther verwendet, der aus dein Hydrochlorid desselben er halten wurde. A method according to claim and the dependent claims 1 to 4, characterized in that 1-Naphtogy acetiminoethyl ether is used for the implementation, which was obtained from the hydrochloride of the same.
CH204745D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204745A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204745T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204745A true CH204745A (en) 1939-05-15

Family

ID=25723398

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204745D CH204745A (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) CH204745A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277112A (en) * 1963-09-20 1966-10-04 Ciba Geigy Corp Phenoxy 2-(1, 3-diaza-2-cycloalkenyl)compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3277112A (en) * 1963-09-20 1966-10-04 Ciba Geigy Corp Phenoxy 2-(1, 3-diaza-2-cycloalkenyl)compounds

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