CH301689A - Process for the preparation of a new aromatic thioether. - Google Patents

Process for the preparation of a new aromatic thioether.

Info

Publication number
CH301689A
CH301689A CH301689DA CH301689A CH 301689 A CH301689 A CH 301689A CH 301689D A CH301689D A CH 301689DA CH 301689 A CH301689 A CH 301689A
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 CH301689A publication Critical patent/CH301689A/en

Links

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)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (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-benzyl-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  
EMI0001.0010     
    eine Verbindung der Formel  
EMI0001.0011     
    einwirken lässt, wobei     Y    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 Basisehen Kon  densationsmittels mit einer     Verbindung    der  Formel     1I    umzusetzen.    Der auf diese Weise erhaltene     2,4-Dioxy-          phenyl-benzyl-thioäther    bildet ein unter  0,02 mm bei 140 bis 145  siedendes, farbloses  Öl, welches nach einiger Zeit zu weissen Kri  stallen erstarrt, die bei 86 bis 87  schmelzen.  <I>Beispiel:</I>  20,0 g     2,4-Dioxy-thiophenol    werden in einer  Lösung von 3,24 g Natrium in 200     cm3    Äthanol  mit 20,0 g     Benzylchlorid    4 Stunden auf dem  Wasserbad erhitzt.

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



  Man erhält so 19,0 g (das sind 58,5 % der  Theorie) des unter 0,02 mm bei 140 bis 145   siedenden     2,4-Dioxy-phenyl-benzyl-thioäthers,     welcher nach einigem Stehen kristallin wird  und dann bei 86 bis 87  schmilzt.  



  Die Verbindung ist unlöslich in Wasser  und     Petroläther;    schlecht löslich in Benzol;  gut löslich in Äthanol, Aceton,     Dioxan,    Essig  ester, Äther und Chloroform.



  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-benzyl-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
EMI0001.0010
    a compound of the formula
EMI0001.0011
    can act, Y and Y being radicals which 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-dioxyphenylbenzyl thioether obtained in this way forms a colorless oil which boils below 0.02 mm at 140 to 145 and which solidifies after some time into white crystals which melt at 86 to 87. <I> Example: </I> 20.0 g of 2,4-dioxy-thiophenol are heated in a solution of 3.24 g of sodium in 200 cm3 of ethanol with 20.0 g of benzyl chloride for 4 hours on a water bath.

   The alcohol is then distilled off, absorbed in ether and shaken well with water. After drying, the ether is distilled off and the residue was fractionated in vacuo.



  19.0 g (that is 58.5% of theory) of the 2,4-dioxy-phenylbenzyl-thioether boiling below 0.02 mm at 140 to 145, which becomes crystalline after standing for a while and then at 86 are obtained until 87 melts.



  The compound is insoluble in water and petroleum ether; poorly soluble in benzene; Soluble in ethanol, acetone, dioxane, ethyl acetate, ether and chloroform.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen aromatischen Thioäthers, dadurch gekenn zeichnet, dass man auf eine Verbindung der Formel EMI0001.0035 eine Verbindung der Formel EMI0002.0001 einwirken lässt, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten. PATENT CLAIM: Process for the production of a new aromatic thioether, characterized in that one uses a compound of the formula EMI0001.0035 a compound of the formula EMI0002.0001 can act, where X and Y are radicals splitting off during the reaction. Der auf diese Weise erhaltene 2,4-Dioxy-phenyl-benzyl- thioäther bildet ein unter 0,02 mm bei 140 bis 145 C siedendes, farbloses Öl, das nach kurzem Stehen erstarrt und dann bei 86 bis 87 schmilzt. Der neue Thioäther soll als Chemo- therapeuticum Verwendung finden. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man eine Verbindung der Formel I mit einem Benzyl-halogenid umsetzt. The 2,4-dioxyphenylbenzyl thioether obtained in this way forms a colorless oil which boils below 0.02 mm at 140 to 145 C, which solidifies after standing for a short time and then melts at 86 to 87. The new thioether is to be used as a chemotherapeutic agent. SUBSTANTIAL CLAIM Process according to patent claim, characterized in that a compound of formula I is reacted with a benzyl halide.
CH301689D 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether. CH301689A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH301689T 1951-08-07
CH297993T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301689A true CH301689A (en) 1954-09-15

Family

ID=25733924

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301689D CH301689A (en) 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether.

Country Status (1)

Country Link
CH (1) CH301689A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009958A (en) * 1957-06-06 1961-11-21 Polaroid Corp Hydroquinonyl derivatives and their synthesis

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3009958A (en) * 1957-06-06 1961-11-21 Polaroid Corp Hydroquinonyl derivatives and their synthesis

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