CH301697A - Process for the preparation of a new aromatic thioether. - Google Patents

Process for the preparation of a new aromatic thioether.

Info

Publication number
CH301697A
CH301697A CH301697DA CH301697A CH 301697 A CH301697 A CH 301697A CH 301697D A CH301697D A CH 301697DA CH 301697 A CH301697 A CH 301697A
Authority
CH
Switzerland
Prior art keywords
thioether
compound
formula
preparation
new aromatic
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Cilag
Original Assignee
Cilag Ag
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 Cilag Ag filed Critical Cilag Ag
Publication of CH301697A publication Critical patent/CH301697A/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C333/02—Monothiocarbamic acids; Derivatives thereof

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  Verfahren     zur    Herstellung eines neuen aromatischen     Thioäthers.       Das vorliegende Patent bezieht sich auf  ein Verfahren zur Herstellung eines neuen  aromatischen     Thioäthers,    nämlich des     2,4-          Dioxy-phenyl-phenoxyäthyl-thioäthers.     



  Dieser     Thioäther    hat eine starke Hemm  wirkung auf das Bakterienwachstum sowie  eine gewisse v     ermicide    Wirkung und soll als       Chemotherapeuticum    Verwendung finden.  



  Das erfindungsgemässe Verfahren zur Her  stellung des neuen aromatischen     Thioäthers     ist dadurch gekennzeichnet, dass man auf eine  Verbindung der Formel  
EMI0001.0010     
    eine Verbindung der Formel  
EMI0001.0011     
    einwirken lässt, wobei X und Y sieh bei der  Reaktion abspaltende Reste bedeuten.  



  Man kann beispielsweise auf ein Metall  salz des     2,4-Dioxy-thiophenols    (X =     Me,    z. B.  Natrium, Kalium usw.) eine Verbindung der  Formel     II    einwirken lassen, in welcher Y ein  Halogenatom oder einen andern sich leicht  abspaltenden Rest, wie z. B. einen     Alkyl-    oder       Aryl-sulfonyloxyrest,    bedeutet.  



  Es ist weiter auch möglich, das     2,4-Dioxy-          thiophenol    in Gegenwart eines basischen Kon  densationsmittels mit einer Verbindung der  Formel     II    umzusetzen.    Der auf diese Weise erhaltene     2,4-Dioxy-          phenyl-phenoxyäthyl-thioäther    bildet farblose  Kristalle, die bei 106 bis 108  schmelzen.         Beispiel:     3,2 g Natrium werden in 200     cm3        abs.     



       Äthanol    gelöst. Die Lösung wird mit<B>20g</B>       2,4-Dioxy-thiophenol    versetzt und unter Rüh  ren 28,4 g     Phenoxyäthylbromid    zugefügt.  Man lässt 20 Stunden bei Zimmertemperatur  stehen, kocht dann noch 3 Stunden auf dem  Dampfbad und verdampft anschliessend zur  Trockne. Der Rückstand wird in Äther auf  genommen, die ätherische Lösung mit Wasser  gewaschen, über Natriumsulfat getrocknet und  wieder     verdampft.    Der     Rückstand    wird aus  Chlorbenzol umkristallisiert, wobei man den  bei 106 bis 108  schmelzenden     2,4-Dioxy-phe-          nyl-phenoxyäthyl-thioäther    in Form weisser  Kristalle in einer Ausbeute von 68,5 % ge  winnt.  



  Die neue Verbindung löst sich gut in Ace  ton,     Dioxan,    Essigester, Äther,     wenig.in    kaltem  Wasser und     Petroläther.  



  Process for the preparation of a new aromatic thioether. The present patent relates to a process for the preparation of a new aromatic thioether, namely 2,4-dioxy-phenyl-phenoxyethyl-thioether.



  This thioether has a strong inhibitory effect on bacterial growth and a certain verminicidal effect and is said to be used as a chemotherapeutic agent.



  The process according to the invention for preparing the new aromatic thioether is characterized in that a compound of the formula
EMI0001.0010
    a compound of the formula
EMI0001.0011
    lets act, where X and Y see in the reaction represent splitting residues.



  For example, a compound of formula II in which Y is a halogen atom or another easily split off radical can act on a metal salt of 2,4-dioxy-thiophenol (X = Me, e.g. sodium, potassium, etc.) such as B. is an alkyl or aryl sulfonyloxy radical.



  It is also possible to react the 2,4-dioxythiophenol in the presence of a basic condensation agent with a compound of the formula II. The 2,4-dioxyphenyl-phenoxyethyl-thioether obtained in this way forms colorless crystals which melt at 106-108. Example: 3.2 g sodium are in 200 cm3 abs.



       Dissolved ethanol. The solution is mixed with <B> 20 g </B> 2,4-dioxy-thiophenol and 28.4 g of phenoxyethyl bromide are added with stirring. It is left to stand for 20 hours at room temperature, then cooked for 3 hours on the steam bath and then evaporated to dryness. The residue is taken up in ether, the ethereal solution is washed with water, dried over sodium sulfate and evaporated again. The residue is recrystallized from chlorobenzene, whereupon the 2,4-dioxyphenylphenoxyethyl thioether, which melts at 106 to 108, is won in the form of white crystals in a yield of 68.5%.



  The new compound dissolves well in acetone, dioxane, ethyl acetate, ether, little in cold water and petroleum ether.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen aromatischen Thioäthers, dadurch gekenn zeichnet, dass man auf eine Verbindung der Formel EMI0001.0036 eine Verbindung der Formel EMI0002.0001 einwirken lässt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten. Der auf diese Weise erhaltene 2,4-Dioxy-phenyl-phen- oxyäthyl-thioäther bildet farblose Kristalle, die bei 106 bis 108 schmelzen. Der neue Thioäther soll als Chemothera- peuticum Verwendung finden. PATENT CLAIM: Process for the production of a new aromatic thioether, characterized in that one uses a compound of the formula EMI0001.0036 a compound of the formula EMI0002.0001 can act, where X and Y are radicals splitting off during the reaction. The 2,4-dioxy-phenyl-phenoxyethyl-thioether obtained in this way forms colorless crystals which melt at 106-108. The new thioether is said to be used as a chemotherapeutic. UNTERANSPRUCH: Verfahren nach Patentansprueh, dadureh gekennzeichnet, da.ss man eine Verbindung der Formel I mit einem Phenoxy-äthyl-halogenid umsetzt. SUBCLAIM: Process according to patent claim, characterized by the fact that a compound of formula I is reacted with a phenoxyethyl halide.
CH301697D 1951-11-16 1951-11-16 Process for the preparation of a new aromatic thioether. CH301697A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH301697T 1951-11-16
CH297993T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301697A true CH301697A (en) 1954-09-15

Family

ID=25733932

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301697D CH301697A (en) 1951-11-16 1951-11-16 Process for the preparation of a new aromatic thioether.

Country Status (1)

Country Link
CH (1) CH301697A (en)

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