CH301691A - Process for the preparation of a new aromatic thioether. - Google Patents

Process for the preparation of a new aromatic thioether.

Info

Publication number
CH301691A
CH301691A CH301691DA CH301691A CH 301691 A CH301691 A CH 301691A CH 301691D A CH301691D A CH 301691DA CH 301691 A CH301691 A CH 301691A
Authority
CH
Switzerland
Prior art keywords
sep
thioether
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 CH301691A publication Critical patent/CH301691A/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     aro-          matisehen        Thioäthers,    nämlich des     2,4-Dioxy-          plienyl-i-butyl-thioäthers.     



  Dieser     Thioäther    hat eine starke Hemmwir  kung auf das Bakterienwachstum sowie eine       @Olewisse    v     ermicide    Wirkung und soll als     Chemo-          iherapeuticum    Verwendung finden.  



  Das erfindungsgemässe Verfahren zur     Her-          tellung    des neuen aromatischen     Thioäthers     ist dadurch gekennzeichnet, dass man auf eine       Verbindung    der Formel  
EMI0001.0016     
    eine Verbindung der Formel  
EMI0001.0017     
    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-srtlfonyloxyrest,    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-i-butyl-thioäther    bildet ein unter  0;06     mm    bei 113 bis 115  siedendes, farbloses  öl.  



       Beispiel:     20,0 g     2,4-Dioxy-thiophenol    werden in einer  Lösung von 3,23 g Natrium in 200     cm3    Äthanol  mit 20,0 g     iso-Butylbromid    3 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  Rückstand im Vakuum fraktioniert.  



  Man erhält so 22,0 g (das sind 78,9 % der  Theorie) des unter 0,06 mm bei 113 bis 115   siedenden     2,4-Dioxy-phenyl-i-butyl-thioäthers.     Farbloses Öl, unlöslich in Wasser, verdünnter  Salzsäure und     Petroläther;    gut     löslich    in ver  dünnter Natronlauge; 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 production of a new aromatic thioether, namely 2,4-dioxyplienyl-i-butyl-thioether.



  This thioether has a strong inhibitory effect on bacterial growth and an @Olewisse v ermicide effect and is said to be used as a chemotherapeutic agent.



  The process according to the invention for the production of the new aromatic thioether is characterized in that one refers to a compound of the formula
EMI0001.0016
    a compound of the formula
EMI0001.0017
    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. an alkyl or aryl-srtlfonyloxyest means. 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-i-butyl-thioether obtained in this way forms a colorless oil boiling below 0.06 mm at 113 to 115.



       Example: 20.0 g of 2,4-dioxy-thiophenol are heated in a solution of 3.23 g of sodium in 200 cm3 of ethanol with 20.0 g of isobutyl bromide on a water bath for 3 hours. The alcohol is then distilled off, absorbed in ether and shaken well with water. After drying, the ether is distilled off and the residue is fractionated in vacuo.



  This gives 22.0 g (that is 78.9% of theory) of 2,4-dioxy-phenyl-i-butyl-thioether which boils below 0.06 mm at 113 to 115. Colorless oil, insoluble in water, dilute hydrochloric acid and petroleum ether; easily soluble in dilute sodium hydroxide solution; miscible with ethanol, acetone, dioxane, ethyl acetate, ether, chloroform and benzene.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen aro matischen Thioäthers, dadurch gekennzeichnet, dass man auf eine Verbindung der Formel EMI0001.0040 eine Verbindung der Formel EMI0002.0001 EMI0002.0002 einwirken <SEP> lässt, <SEP> wobei <SEP> X <SEP> und <SEP> Y <SEP> siel. <SEP> bei <SEP> dei# <tb> Reaktion <SEP> abspaltende <SEP> Peste <SEP> bedeuten. <SEP> Der <tb> auf <SEP> diese <SEP> Weise <SEP> erhaltene <SEP> 2,.1-Dioxy-plienyl-i- EMI0002.0003 butyl-thioäther <SEP> bildet <SEP> ein <SEP> unter <SEP> 0,06 <SEP> mm <SEP> bei <tb> l.13 <SEP> bis <SEP> 115 <SEP> C <SEP> siedendes, <SEP> farbloses <SEP> Öl. PATENT CLAIM: Process for the preparation of a new aromatic thioether, characterized in that a compound of the formula EMI0001.0040 a compound of the formula EMI0002.0001 EMI0002.0002 <SEP> has an effect, <SEP> where <SEP> X <SEP> and <SEP> Y <SEP> fell. <SEP> at <SEP> dei # <tb> reaction <SEP> means separating <SEP> pests <SEP>. <SEP> The <tb> <SEP> this <SEP> way <SEP> obtained <SEP> 2, .1-Dioxy-plienyl-i- EMI0002.0003 butyl thioether <SEP> forms <SEP> a <SEP> under <SEP> 0.06 <SEP> mm <SEP> <tb> l.13 <SEP> to <SEP> 115 <SEP> C <SEP> boiling, <SEP> colorless <SEP> oil. <SEP> Der <tb> neue <SEP> Tliioäther <SEP> soll <SEP> als <SEP> Cheinotherapentieum <tb> Verwendung <SEP> finden. <tb> UNTBP.INSPRI?C'll <tb> Verfahren <SEP> liaeli <SEP> Patentansprueli, <SEP> dadureli <tb> gekennzeiehnet, <SEP> da.ss <SEP> man <SEP> eine <SEP> Verbindung <SEP> der <tb> Formel <SEP> <B>1</B> <SEP> mit <SEP> einem <SEP> i-Btitvl-lialogenic1 <SEP> umsetzt. <SEP> The <tb> new <SEP> Tliioether <SEP> should <SEP> as <SEP> Cheinotherapentieum <tb> Find use <SEP>. <tb> UNTBP.INSPRI? c'll <tb> Procedure <SEP> liaeli <SEP> patent claims, <SEP> dadureli <tb> marked, <SEP> da.ss <SEP> man <SEP> a <SEP> connection <SEP> the <tb> Formula <SEP> <B> 1 </B> <SEP> with <SEP> a <SEP> i-Btitvl-lialogenic1 <SEP> implements.
CH301691D 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether. CH301691A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH301691T 1951-08-07
CH297993T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301691A true CH301691A (en) 1954-09-15

Family

ID=25733926

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301691D CH301691A (en) 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether.

Country Status (1)

Country Link
CH (1) CH301691A (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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