CH146712A - Process for the preparation of hydroquinone-B-guanidinoethyl-phenyl ether. - Google Patents

Process for the preparation of hydroquinone-B-guanidinoethyl-phenyl ether.

Info

Publication number
CH146712A
CH146712A CH146712DA CH146712A CH 146712 A CH146712 A CH 146712A CH 146712D A CH146712D A CH 146712DA CH 146712 A CH146712 A CH 146712A
Authority
CH
Switzerland
Prior art keywords
hydroquinone
guanidinoethyl
phenyl ether
preparation
ether
Prior art date
Application number
Other languages
German (de)
Inventor
F Hoffmann- Aktiengesellschaft
Original Assignee
Hoffmann La Roche
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 Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of CH146712A publication Critical patent/CH146712A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren zur Herstellung von     Hydrochinon-R-guanidinoäthyl-phenyläther.       Die     Aryläther    der     Oxyalkylguanidine     der allgemeinen Formel:  
EMI0001.0004     
    wobei Ar den Rest eines ein- oder mehr  kernigen     iso-    oder     heterozyklischen    Kohlen  wasserstoffes, R = einen     Alkylrest    bedeuten,  sind bis jetzt nicht beschrieben.  



  Gegenstand der Erfindung ist ein Ver  fahren zur Herstellung von     Ilydrochinon-ss-          guanidinoäthyl-phenyläther,    welches dadurch  gekennzeichnet ist, dass man     Hydrochinon-          phenyl-ss-bromäthyläther    auf     Guanidin    ein  wirken lässt.  



  Der     Hydrochinon-ss-guanidinoäthyl-phe-          nyläther    bildet ein kristallinisches     Hydro-          bromid,    welches bei 141' schmilzt und in  Wasser schwer, in Alkohol leichter löslich  ist. Das Hydrochlorid des     Hydrochinon-ss-          guanidinoäthyl-phenyläthers    schmilzt bei    130  . Ein Teil davon löst sich in etwa 300  Teilen Wasser. Die neue Verbindung soll  als Desinfektionsmittel für Menschen ver  wendet werden.

      <I>Beispiel:</I>  Zu einer Lösung von 11;8 Teilen     Gua-          nidin    in 200 Teilen absolutem Alkohol setzt  man 7,3 Teile     Hydrochinonphenyl-ss-brom-          äthyläther    (aus     Hydrochinonphenyläther-          Natrium    und überschüssigem     Äthylendibro-          mid    erhalten) und lässt sechs Stunden unter       Rückfluss    sieden. Hierauf verdampft man  den Alkohol im Vakuum. nimmt den Rück  stand in Wasser und Benzol auf, trennt von  Wasser und     destilliert    das mit Natrium  sulfat getrocknete Benzol ab.

   Den Rückstand  löst man in der berechneten Menge verdünn  ter     Bromwasserstoffsäure    und wäscht mit  Äther, wobei sich das     Hy        drobromid    als  schweres 01, das langsam kristallinisch wird.  aus der wässerigen Schicht bald abscheidet.      Aus     Alkohol-Ather    umkristallisiert schmilzt  das Salz bei 141  .



  Process for the preparation of hydroquinone-R-guanidinoethyl-phenyl ether. The aryl ethers of the oxyalkylguanidines of the general formula:
EMI0001.0004
    where Ar is the radical of a mono- or more nuclear iso- or heterocyclic hydrocarbon, R = an alkyl radical, have not yet been described.



  The invention relates to a process for the preparation of Ilydroquinone-ss-guanidinoethyl-phenyl ether, which is characterized in that hydroquinone-phenyl-ss-bromoethyl ether is allowed to act on guanidine.



  The hydroquinone-ß-guanidinoethyl-phenyl ether forms a crystalline hydrobromide which melts at 141 ° and is sparingly soluble in water and more easily soluble in alcohol. The hydrochloride of the hydroquinone-ss- guanidinoethyl-phenyl ether melts at 130. Some of it dissolves in about 300 parts of water. The new compound is intended to be used as a disinfectant for humans.

      <I> Example: </I> To a solution of 11; 8 parts of guanidine in 200 parts of absolute alcohol, 7.3 parts of hydroquinone phenyl-ss-bromo-ethyl ether (obtained from sodium hydroquinone-phenyl ether and excess ethylenedibromide) are added. and reflux for six hours. The alcohol is then evaporated in vacuo. takes up the residue in water and benzene, separates from water and distilled off the benzene dried with sodium sulfate.

   The residue is dissolved in the calculated amount of dilute hydrobromic acid and washed with ether, whereby the hydrobromide turns out to be heavy oil that slowly becomes crystalline. soon separates from the watery layer. Recrystallized from alcohol-ether, the salt melts at 141.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von Hydro- chinon - ss - guanidinoäthyl-phenyläther, da durch gekennzeichnet, dass man Hydrochinon- phenyl-ss-bromäthyläther auf Guanidin ein wirken lässt. Der ]Elydrochinon-ss-guanidinoäthyl-phe- nyläther bildet ein kristallinisches Hydro- bromid, welches bei 141 schmilzt und in Wasser schwer, in Alkohol leichter löslich ist. PATENT CLAIM: Process for the preparation of hydroquinone - ss - guanidinoethyl-phenyl ether, characterized in that hydroquinone-phenyl-ss-bromoethyl ether is allowed to act on guanidine. The] elydroquinone-SS-guanidinoethyl-phenyl ether forms a crystalline hydrobromide which melts at 141 and is sparingly soluble in water and more easily soluble in alcohol. Das Ilydrochlorid des Ilydrochinon-ss- guanidinoäthyl-phenyläthers schmilzt bei 130 . Ein Teil davon löst sich in etwa 300 Teilen Wasser. Die neue Verbindung soll als Des infektionsmittel für Menschen verwendet werden. The Ilydrochlorid of Ilydroquinon-ss- guanidinoäthylphenyläthers melts at 130. Some of it dissolves in about 300 parts of water. The new compound is intended to be used as a disinfectant for humans.
CH146712D 1930-01-11 1930-01-11 Process for the preparation of hydroquinone-B-guanidinoethyl-phenyl ether. CH146712A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH146712T 1930-01-11

Publications (1)

Publication Number Publication Date
CH146712A true CH146712A (en) 1931-04-30

Family

ID=4402876

Family Applications (1)

Application Number Title Priority Date Filing Date
CH146712D CH146712A (en) 1930-01-11 1930-01-11 Process for the preparation of hydroquinone-B-guanidinoethyl-phenyl ether.

Country Status (1)

Country Link
CH (1) CH146712A (en)

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