CH301695A - Process for the preparation of a new aromatic thioether. - Google Patents

Process for the preparation of a new aromatic thioether.

Info

Publication number
CH301695A
CH301695A CH301695DA CH301695A CH 301695 A CH301695 A CH 301695A CH 301695D A CH301695D A CH 301695DA CH 301695 A CH301695 A CH 301695A
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 CH301695A publication Critical patent/CH301695A/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 aroma  tischen     Thioäthers,    nämlich des     2,4-Dioxy-          phenyl-        (ss-phenoxyäthoxy-äthyl)        -thioäthers.     



  Dieser     Thioäther    hat eine starke Hemm  wirkung auf das Bakterienwachstum sowie  eine     gewisse        vermicide    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  
EMI0001.0015     
    eine Verbindung der Formel  
EMI0001.0016     
    einwirken lässt, wobei X und Y sich 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-        (ss-phenoxy-äthoxy-äthyl)        -thioäther     bildet farblose Kristalle, welche bei 68 bis 69        schmelzen.     



       Beispiel:     200 g     2,4-Dioxy-thiophenol    werden     in        einer     Lösung von 32 g Natrium in 2 Litern     abs.     Äthanol aufgeschlämmt und das Ganze bis zur  Lösung schwach erwärmt.

   In die hellgelbe       klare    Lösung werden 284 g     ss-Phenoxyäthoxy-          äthylchlorid    in 400     cms        abs.        Äthänol        zuge-          tropft.    Man lässt 20 Stunden bei Zimmertem  peratur stehen, erhitzt dann noch 2     Stunden     auf dem Dampfbad, destilliert den     Alkohol    ab       Lind    nimmt den     Rückstand    in Äther auf. Die  ätherische Lösung wird mit Wasser ausge  zogen, dann über Natriumsulfat getrocknet  und auf dem Wasserbad verdampft.

   Der 350 g  wiegende Rückstand wird im Hochvakuum  destilliert, wobei man ein gelbliches, zähflüs  siges Öl erhält, das unter 0,06 mm bei 187  bis 188  überdestilliert. Dieses Öl kristalli  siert nach längerem Stehen und kann aus  Chlorbenzol umkristallisiert werden, wobei  man den bei 68 bis 69  schmelzenden     2,4-Dioxy-          phenyl-(ss-phenoxyäthoxy-äthyl)-thioäther    er-.  hält. Die Ausbeute beträgt 275 g, das sind  64 % der Theorie. Die neue     Verbindung    löst  sich sehr gut in Äthanol, Aceton,     Dioxan,     Essigester, Äther, Chloroform und Benzol;  sehr wenig löst sie sich in kochendem Wasser  und in     Petroläther.  



  Process for the preparation of a new aromatic thioether. The present patent relates to a process for the production of a new aromatic thioether, namely the 2,4-dioxyphenyl (ss-phenoxyethoxy-ethyl) thioether.



  This thioether has a strong inhibitory effect on bacterial growth as well as a certain vermicidal 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
EMI0001.0015
    a compound of the formula
EMI0001.0016
    can act, where X and Y are radicals splitting off during the reaction.



  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 with a compound of the formula II in the presence of a basic condensing agent.



  The 2,4-dioxyphenyl (ss-phenoxy-ethoxy-ethyl) -thioether obtained in this way forms colorless crystals which melt at 68-69.



       Example: 200 g of 2,4-dioxy-thiophenol are dissolved in a solution of 32 g of sodium in 2 liters of abs. Slurried ethanol and warmed the whole thing gently until dissolved.

   284 g of β-phenoxyethoxyethyl chloride in 400 cms of abs are added to the light yellow clear solution. Ethanol was added dropwise. It is left to stand for 20 hours at room temperature, then heated on the steam bath for 2 hours, the alcohol is distilled off and the residue is taken up in ether. The ethereal solution is drawn out with water, then dried over sodium sulfate and evaporated on a water bath.

   The residue, which weighs 350 g, is distilled in a high vacuum, giving a yellowish, viscous oil which distills over at 187 to 188 under 0.06 mm. This oil crystallizes after prolonged standing and can be recrystallized from chlorobenzene, whereby the 2,4-dioxyphenyl- (s-phenoxyethoxy-ethyl) -thioether which melts at 68 to 69 is obtained. holds. The yield is 275 g, which is 64% of theory. The new compound dissolves very well in ethanol, acetone, dioxane, ethyl acetate, ether, chloroform and benzene; it dissolves very little in boiling water and in petroleum ether.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstelliuig eines neuen aromatischen Thioäthers, dadurch gekenn zeichnet, dass man auf eine Verbindung der Formel EMI0002.0003 eine Verbindung der Formel EMI0002.0004 einwirken lässt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten. Der auf diese Weise erhaltene 2,4-Dioxy-phenyl-(ss- phenoxyäthoxy-äthyl)-thioäther bildet farb lose Kristalle, welche bei 68 bis 69 schmelzen. Der neue Thioäther soll als Chemothera- peuticiun Verwendung finden. PATENT CLAIM: Process for the production of a new aromatic thioether, characterized in that a compound of the formula EMI0002.0003 a compound of the formula EMI0002.0004 can act, where X and Y are radicals splitting off during the reaction. The 2,4-dioxy-phenyl (ss-phenoxyethoxy-ethyl) thioether obtained in this way forms colorless crystals which melt at 68-69. The new thioether is said to be used as a chemotherapeutic. UNTERANSPRUCH: Verfahren nach Patentansprueh, dadurch gekennzeichnet, dass man eine Verbindung der Formel I mit einem ss-Phenoxyäthoxy-äthyl- halogenid umsetzt. SUBCLAIM: Process according to patent claim, characterized in that a compound of the formula I is reacted with an β-phenoxyethoxy-ethyl halide.
CH301695D 1951-11-16 1951-11-16 Process for the preparation of a new aromatic thioether. CH301695A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH297993T 1951-11-16
CH301695T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301695A true CH301695A (en) 1954-09-15

Family

ID=25733930

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301695D CH301695A (en) 1951-11-16 1951-11-16 Process for the preparation of a new aromatic thioether.

Country Status (1)

Country Link
CH (1) CH301695A (en)

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