CH301688A - Process for the preparation of a new aromatic thioether. - Google Patents

Process for the preparation of a new aromatic thioether.

Info

Publication number
CH301688A
CH301688A CH301688DA CH301688A CH 301688 A CH301688 A CH 301688A CH 301688D A CH301688D A CH 301688DA CH 301688 A CH301688 A CH 301688A
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 CH301688A publication Critical patent/CH301688A/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

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (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-n-hexyl-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  
EMI0001.0011     
    eine Verbindung der Formel       CH3-CH2-CH2-CH2-CH2-CH2-Y        II     einwirken lässt, wobei X und Y sich bei der  Reaktion abspaltende Reste bedeuten.  



  Man kann beispielsweise auf ein Metallsalz  des     2,4-Dioxy-thiophenols    (X =     Me,    z. B. Na  trium, 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-n-hexyl-thioäther    bildet ein unter  0,07 mm bei 126  siedendes, farbloses Öl.         Beispiel:     15,0 g     2,4-Dioxy-thiophenol    werden in einer  Lösung von 2,42 g Natrium in 150     cm3    Äthanol  mit 18,3 g     n-Hexylbromid    3 Stunden auf dem  Wasserbad erhitzt.

   Darauf destilliert man  den Alkohol ab, nimmt. in Äther auf     und    schüt  telt gut. mit Wasser durch. Nach dem Trock  nen wird der Äther     abdestilliert    und der Rück  stand im Vakuum fraktioniert.  



  Man erhält so 14,0 g (das sind 58,2     %a    der  Theorie) des unter 0,07 mm bei 126  sieden  den     2,4-Dioxy-phenyl-n-hexyl-thioäthers.     



  Farbloses Öl; unlöslich in Wasser,     2n-Salz-          säure    und     Petroläther;    gut löslich in     2n-Na-          tronlauge;    mischbar mit     Äthanol,    Aceton,       Dioxan,    Essigester, Äther, Chloroform und  Benzol.



      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-n-hexyl-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.



  The process according to the invention for preparing the new aromatic thioether is characterized in that a compound of the formula
EMI0001.0011
    a compound of the formula CH3-CH2-CH2-CH2-CH2-CH2-Y II is allowed to act, where X and Y are radicals which are split off during the reaction.



  For example, a compound of the 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-n-hexyl-thioether obtained in this way forms a colorless oil boiling below 0.07 mm at 126. Example: 15.0 g of 2,4-dioxy-thiophenol are heated in a solution of 2.42 g of sodium in 150 cm3 of ethanol with 18.3 g of n-hexyl bromide on a water bath for 3 hours.

   The alcohol is then distilled off and taken. in ether and shakes well. with water through. After the dry NEN, the ether is distilled off and the residue was fractionated in vacuo.



  14.0 g (that is 58.2% of theory) of the 2,4-dioxy-phenyl-n-hexyl-thioether boiling below 0.07 mm at 126 are obtained in this way.



  Colorless oil; insoluble in water, 2N hydrochloric acid and petroleum ether; readily soluble in 2N sodium hydroxide solution; miscible with ethanol, acetone, dioxane, ethyl acetate, ether, chloroform and benzene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen aromatischen Thioäthers, dadurch gekenn zeichnet, dass man auf eine Verbindung der Formel EMI0001.0041 eine Verbindung der Formel CH3-CH2-CH2-CH2-CH2-CH2-Y II einwirken lässt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten. Der auf diese Weise erhaltene 2,4-Dioxy-phenyl-n- hexyl-thioäther bildet ein unter 0,07 mm bei 126 C siedendes, farbloses Öl. Der neue Thio- äther soll als Chemotherapeuticum Verwen dung finden. PATENT CLAIM: Process for the production of a new aromatic thioether, characterized in that one uses a compound of the formula EMI0001.0041 a compound of the formula CH3-CH2-CH2-CH2-CH2-CH2-Y II is allowed to act, where X and Y are radicals which are split off during the reaction. The 2,4-dioxyphenyl-n-hexyl-thioether obtained in this way forms a colorless oil boiling below 0.07 mm at 126.degree. The new thioether is said to be used as a chemotherapeutic agent. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man eine Verbindung der Formel 1 mit einem n-Hexyl-halogenid umsetzt. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a compound of formula 1 is reacted with an n-hexyl halide.
CH301688D 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether. CH301688A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH301688T 1951-08-07
CH297993T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301688A true CH301688A (en) 1954-09-15

Family

ID=25733923

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301688D CH301688A (en) 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether.

Country Status (1)

Country Link
CH (1) CH301688A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5013756A (en) * 1985-09-26 1991-05-07 Societe De Conseils De Recherches Et D'application Scientifiques (S.C.R.A.S) Catechol derivatives, a process of preparation thereof, and therapeutical compositions containing the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5013756A (en) * 1985-09-26 1991-05-07 Societe De Conseils De Recherches Et D'application Scientifiques (S.C.R.A.S) Catechol derivatives, a process of preparation thereof, and therapeutical compositions containing the same

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