CH301687A - Process for the preparation of a new aromatic thioether. - Google Patents

Process for the preparation of a new aromatic thioether.

Info

Publication number
CH301687A
CH301687A CH301687DA CH301687A CH 301687 A CH301687 A CH 301687A CH 301687D A CH301687D A CH 301687DA CH 301687 A CH301687 A CH 301687A
Authority
CH
Switzerland
Prior art keywords
thioether
compound
formula
preparation
amyl
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 CH301687A publication Critical patent/CH301687A/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

  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  <B>Verfahren</B>     zur        Herstellung        eines   <B>neuen</B>     aromatischen        Thioäthers.       Das vorliegende Patent bezieht sich auf  ein Verfahren zur Herstellung eines neuen  aromatischen     Thioäthers,    nämlich des     2,4-          Dioxy-phenyl-i-amyl-thioäthers.     



  Dieser     Thioäther    hat eine starke Hemm  wirkung auf das     Bakterienwachstum    sowie  eine gewisse     vermicide    Wirkung und soll als       Chemotherapeu.ticum    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-i-amyl-thioäther    bildet ein unter  0,01 mm bei 120 bis 122  siedendes, farbloses  Öl.  



  <I>Beispiel:</I>  25,0 g     2,4-Dioxy-thiophenol    werden in einer  Lösung von 4,05 g Natrium in 250     cm3     Äthanol mit 27,1 g     iso-Amylbromid    3 Stun  den auf dem Wasserbad erhitzt. Darauf de  stilliert 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 30,0 g (das sind 80,5 % der  Theorie) des unter 0,01 mm bei 120 bis 122   siedenden     2,4-Dioxy-phenyl-i-amyl-thioäthers.     



  Farbloses Öl; unlöslich in Wasser, verdünn  ter Salzsäure und     Petroläther;    gut     löslich    in  verdünnter Natronlauge; mischbar mit Äthanol,  Aceton,     Dioxan,    Essigester, Äther, Chloroform  und     Benzol.  



  <B> Process </B> for the production of a <B> new </B> aromatic thioether. The present patent relates to a process for the preparation of a new aromatic thioether, namely 2,4-dioxy-phenyl-i-amyl-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 chemotherapeu.ticum.



  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 condensation agent.



  The 2,4-dioxyphenyl-i-amyl-thioether obtained in this way forms a colorless oil boiling below 0.01 mm at 120 to 122 mm.



  <I> Example: </I> 25.0 g of 2,4-dioxy-thiophenol are heated in a solution of 4.05 g of sodium in 250 cm3 of ethanol with 27.1 g of iso-amyl bromide for 3 hours on a water bath. The alcohol is then distilled, absorbed in ether and shaken well with water. After drying, the ether is distilled off and the residue is fractionated in vacuo.



  30.0 g (that is 80.5% of theory) of the 2,4-dioxy-phenyl-i-amyl thioether boiling below 0.01 mm at 120 to 122 are obtained in this way.



  Colorless oil; insoluble in water, dilute hydrochloric acid and petroleum ether; readily 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 aromatischen Thioäthers, dadurch gekenn zeichnet, dass man auf eine Verbindung der Formel EMI0001.0041 eine Verbindung der Formel EMI0002.0001 einwirken lässt, wobei X und Y sieh bei der Reaktion abspaltende Reste bedeuten. Der auf diese Weise erhaltene 2,4-Dioxy-phenyl-i- amyl-thioäther bildet ein unter 0,01 mm bei 120 bis 122 C siedendes, farbloses Öl. Der neue Thioäther soll als Chemotherapeutieum Verwendung 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 EMI0002.0001 lets act, where X and Y see in the reaction represent splitting residues. The 2,4-dioxy-phenyl-i-amyl-thioether obtained in this way forms a colorless oil boiling below 0.01 mm at 120 to 122 ° C. The new thioether is said to be used as chemotherapy. UNTERÄNSPRU CIII Verfahren naeh Patentansprueh, dadureh: gekennzeiehnet, dass man eine Verbindung der Formel I mit einem iso- Amy l-halogenid um setzt. UNDERTAKING PRU CIII Method according to patent claim, dadureh: it is indicated that a compound of the formula I is reacted with an iso-amyl halide.
CH301687D 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether. CH301687A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH301687T 1951-08-07
CH297993T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301687A true CH301687A (en) 1954-09-15

Family

ID=25733922

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301687D CH301687A (en) 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioether.

Country Status (1)

Country Link
CH (1) CH301687A (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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