CH204730A - 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
CH204730A
CH204730A CH204730DA CH204730A CH 204730 A CH204730 A CH 204730A CH 204730D A CH204730D A CH 204730DA CH 204730 A CH204730 A CH 204730A
Authority
CH
Switzerland
Prior art keywords
ether
reaction
phenylacetimino
dihydride
hydrochloride
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 CH204730A publication Critical patent/CH204730A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms

Landscapes

  • 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,ö).       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung eines in       2-Stellung    substituierten     Imidazoldihydrids-          (4,5),    welches dadurch gekennzeichnet ist,  dass man einen     Phenylacetiminoäther    mit       13exahydro-o-phenylendiamin    umsetzt.  



  Das so gewonnene     2-Benzyl-benzimidazol-          hexahydrid-(4,5,6,7,8,9)    bildet farblose Kri  stalle vom F. 117 bis<B>118'.</B> Sein     Hydro-          chlorid    ist ein farbloses Kristallpulver vom  F. 257  .  



  Die neue Verbindung kann als Arznei  mittel verwendet werden.  



  <I>Beispiel:</I>  Man vermischt eine ätherische Lösung  von 8,5 Teilen     Phenylacetiminoäthyläther          (KI)",    105 bis 106  ) der Formel  
EMI0001.0014     
    mit. 6 Teilen     Hegahydro-o-phenylendiamin            (Kp72o    183 bis     185')    und erwärmt     einige          Stunden    zum Sieden.

   Nach dem     Abdestil-          lieren    des     Lösungsmittels        wird    der Rück  stand im Vakuum bei 50   getrocknet und so  das     2-Benzyl-benzimidazolhexahydrid-(4,5,6,     7,8,9) der Formel  
EMI0001.0025     
    als farbloses     Kristallpulver    erhalten.  



  An Stelle von     Phenylacetiminoäthyläther     kann ebensogut ein anderer Äther, wie z. B.       Methyl-,        Propyl-    oder     Butyläther    Verwen  dung     finden.     



  Statt von der freien Base des     Phenylacet-          iminoäthers    kann man auch vom salzsauren,       bromwasserstoffsauren,    schwefelsauren oder  vom     methylschwefelsauren    Salz derselben  ausgehen.



  Process for the preparation of an imidazole dihydride (4, ö) 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 phenylacetimino ether is reacted with 13exahydro-o-phenylenediamine.



  The 2-benzylbenzimidazole hexahydride (4,5,6,7,8,9) obtained in this way forms colorless crystals from F. 117 to <B> 118 '. </B> Its hydrochloride is colorless Crystal powder from F. 257.



  The new compound can be used as a medicine.



  <I> Example: </I> An ethereal solution of 8.5 parts of phenylacetiminoethyl ether (KI) ", 105 to 106) of the formula is mixed
EMI0001.0014
    With. 6 parts of Hegahydro-o-phenylenediamine (Kp72o 183 to 185 ') and heated to boiling for a few hours.

   After the solvent has been distilled off, the residue is dried in vacuo at 50, and so is the 2-benzylbenzimidazole hexahydride (4,5,6, 7,8,9) of the formula
EMI0001.0025
    obtained as colorless crystal powder.



  Instead of phenylacetiminoethyl ether, another ether, such as e.g. B. methyl, propyl or butyl ether are used.



  Instead of the free base of the phenylacetamide one can also start from the hydrochloric acid, hydrobromic acid, sulfuric acid or the methylsulfuric acid salt thereof.

Claims (1)

PATEN T Abi SPRUCH Verfahren zur Darstellung eines in 2- Stellung substituierten Imidazoldihydrids- (4,5), dadurch gekennzeichnet, dass man einen Phenylacetiminoäther mit Hexahydro- o-phenylendiamin umsetzt. Das so gewonnene 2-Benzylbenzimid- azolhexahydrid-(4,5,6,7,8,9) bildet farblose Kristalle vom F. 117 bis 118 ". Sein Hydro chlorid ist ein farbloses Kristallpulver vom F. 257 . Die neue Verbindung kann als Arznei mittel verwendet werden. PATEN T Abi SPRUCH Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position, characterized in that a phenylacetimino ether is reacted with hexahydro-o-phenylenediamine. The 2-benzylbenzimidazole hexahydride (4,5,6,7,8,9) obtained in this way forms colorless crystals from 117 to 118 ". Its hydrochloride is a colorless crystal powder from 257. The new compound can be used as Medicinal products are used. U:"i TERAX,SPRt CHE 1. Verfahren nach Patentanspruch. dadurch gekennzeichnet, dass man zur Umsetzung Phenylacetiminoäthyläther verwendet. 2. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man zur Umsetzung einen Phenylacetiminoäther verwendet, der aus einem Salz desselben erhalten wurde. 3. Verfahren nach Patentanspruch und Un teranspruch 2, dadurch gekennzeichnet, dass man zur Umsetzung einen Phenyl- acetiminoäther verwendet, der aus einem Hydrohalogenid desselben erhalten wurde. 4. U: "i TERAX, SPRt CHE 1. Process according to patent claim. Characterized in that phenylacetiminoethyl ether is used for the reaction. 2. Process according to patent claim, characterized in that a phenylacetimino ether is used for the reaction which was obtained from a salt thereof. 3 Process according to patent claim and sub-claim 2, characterized in that a phenyl acetimino ether is used for the reaction which was obtained from a hydrohalide of the same. Verfahren nach Patentanspruch und den Unteransprüchen ? und 3, dadurch ge kennzeichnet, dass man zur Umsetzung einen Phenylacetiminoäther verwendet, der aus dem Hydrochlorid desselben erhalten wurde. Verfahren nach Patentanspruch und den Unteransprüchen 1 bis 4, dadurch gekenn zeichnet. dass man zur Umsetzung Phenyl- acetiminoäthyläther verwendet, der aus dein Hydrochlorid desselben erhalten wurde. Method according to patent claim and the subclaims? and 3, characterized in that a phenylacetimino ether is used for the reaction, which was obtained from the hydrochloride of the same. Method according to patent claim and dependent claims 1 to 4, characterized in that. that one uses phenyl acetiminoethyl ether for the reaction, which was obtained from the hydrochloride of the same.
CH204730D 1935-07-23 1935-07-23 Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. CH204730A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH204730T 1935-07-23
CH199906T 1938-09-15

Publications (1)

Publication Number Publication Date
CH204730A true CH204730A (en) 1939-05-15

Family

ID=25723383

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204730D CH204730A (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) CH204730A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325508A (en) * 1963-12-23 1967-06-13 Monsanto Chem Australia Ltd 2-trichloromethyl benzimidazoles

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3325508A (en) * 1963-12-23 1967-06-13 Monsanto Chem Australia Ltd 2-trichloromethyl benzimidazoles

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