CH301684A - Process for the preparation of a new aromatic thioester. - Google Patents

Process for the preparation of a new aromatic thioester.

Info

Publication number
CH301684A
CH301684A CH301684DA CH301684A CH 301684 A CH301684 A CH 301684A CH 301684D A CH301684D A CH 301684DA CH 301684 A CH301684 A CH 301684A
Authority
CH
Switzerland
Prior art keywords
thioester
preparation
compound
formula
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 CH301684A publication Critical patent/CH301684A/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
    • 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        Thioesters.       Das vorliegende Patent bezieht sich auf ein  Verfahren zur Herstellung eines neuen aro  matischen     Thioesters,    nämlich des     2,4-Dioxy-          pheny    1-     (diäthyl-carbaminsäur    e)     -thioesters.     



  Dieser     Thioester    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     Thioesters     ist dadurch gekennzeichnet, dass man auf eine  Verbindung der Formel  
EMI0001.0013     
    eine Verbindung der     Formel     
EMI0001.0015     
    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,     Kalitun    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       Ary1-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-(diäthyl-carbaminsäure)-thioester    bil  det bei 149 bis 150      schmelzende,    weisse Kri  stalle.  



       Beispiel:     14,0 g     2,4-Dioxy-thiophenol    werden     in    einer  Lösung von 2,25 g Natrium in 200     cm3    Äthanol  mit 14,0g     N,N-Diäthyl-carbaminsäurechlorid     1 Stunde auf dem Wasserbad erhitzt. Darauf  destilliert man den Alkohol ab, nimmt in  Äther auf und schüttelt gut mit Wasser durch.  Nach dem Trocknen wird die Ätherlösung  einige -Tage stehengelassen, wobei langsam  eine Fällung entsteht.  



  Durch     Umkristallisieren    aus     Benzol    erhält  man den bei 149 bis 150  schmelzenden     2,4-          Dioxy-phenyl-(diäthyl-carbaminsäure)    -     thio-          ester    in befriedigender Ausbeute.  



  Dieser neue Ester bildet     weisse    Kristalle,  die sich sehr gut in Äthanol, Aceton,     Dioxan,     Essigester und Chloroform lösen und in Was  ser und     Petroläther    unlöslich sind.



  Process for the preparation of a new aromatic thioester. The present patent relates to a process for the preparation of a new aromatic thioester, namely 2,4-dioxypheny 1- (diethylcarbamic acid) thioester.



  This thioester has a strong inhibitory effect on bacterial growth and a certain vermicidal effect and is said to be used as a chemotherapeutic.



  The process according to the invention for preparing the new aromatic thioester is characterized in that a compound of the formula
EMI0001.0013
    a compound of the formula
EMI0001.0015
    can act, where X and Y are radicals splitting 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 Ary1-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 (diethyl carbamic acid) thioester obtained in this way forms white crystals which melt at 149 to 150.



       Example: 14.0 g of 2,4-dioxy-thiophenol are heated in a solution of 2.25 g of sodium in 200 cm3 of ethanol with 14.0 g of N, N-diethylcarbamic acid chloride for 1 hour on a water bath. The alcohol is then distilled off, absorbed in ether and shaken well with water. After drying, the ethereal solution is left to stand for a few days, slowly precipitating.



  Recrystallization from benzene gives the 2,4-dioxy-phenyl- (diethylcarbamic acid) thioester, which melts at 149 to 150, in a satisfactory yield.



  This new ester forms white crystals that dissolve very well in ethanol, acetone, dioxane, ethyl acetate and chloroform and are insoluble in water and petroleum ether.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen aromatischen Thioesters, dadurch gekenn zeichnet, dass man auf eine Verbindung der Formel EMI0001.0046 eine Verbindung der Formel EMI0002.0001 einwirken lä.sst, wobei X und Y sich bei der Reaktion abspaltende Reste bedeuten. Der auf diese Weise erhaltene 2,4-Dioxy-pheny 1 (diäthyl-carba.minsäure)- thioester bildet bei 149 bis 150 C schmelzende, weisse Kristalle. Der neue Thioester soll als Chemotherapeuti- cum Verwendung finden. PATENT CLAIM: Process for the preparation of a new aromatic thioester, characterized in that one is based on a compound of the formula EMI0001.0046 a compound of the formula EMI0002.0001 Lä.sst can act, where X and Y denote residues split off during the reaction. The 2,4-dioxypheny 1 (diethylcarba.mic acid) thioester obtained in this way forms white crystals which melt at 149 to 150.degree. The new thioester is said to be used as a chemotherapeutic agent. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man eine Verbindung der Formel I mit einem Diäthylcarbaminsäure- halogenid umsetzt. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a compound of the formula I is reacted with a diethylcarbamic acid halide.
CH301684D 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioester. CH301684A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH301684T 1951-08-07
CH297993T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301684A true CH301684A (en) 1954-09-15

Family

ID=25733919

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301684D CH301684A (en) 1951-08-07 1951-08-07 Process for the preparation of a new aromatic thioester.

Country Status (1)

Country Link
CH (1) CH301684A (en)

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