CH301702A - Process for the preparation of a new aromatic thioether. - Google Patents

Process for the preparation of a new aromatic thioether.

Info

Publication number
CH301702A
CH301702A CH301702DA CH301702A CH 301702 A CH301702 A CH 301702A CH 301702D A CH301702D A CH 301702DA CH 301702 A CH301702 A CH 301702A
Authority
CH
Switzerland
Prior art keywords
thioether
formula
compound
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 CH301702A publication Critical patent/CH301702A/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
    • 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)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (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)
  • 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 aro  matischen     Thioäthers,    nämlich des     2-Oxy-4-          amino-phenyl-ss-diäthylamino-äthy        1-thioäthers.     



  Dieser     Thioäther    hat eine starke Hemm  wirkung auf das Bakterienwachstum, auf das  Wachstum von Pilzen sowie eine gewisse     ver-          micideWirkung    und soll als     Chemotherapeuti-          cum    und     Antimycoticum    Verwendung finden.  



  Das erfindungsgemässe Verfahren zur Her  stellung 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-Oxy-4-amino-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.     Alkyl-    oder       Aryl-sulfonyloxyrest,    bedeutet.    Es ist weiter auch möglich, das     2-Oxy-4-          amino-thiophenol    in Gegenwart     eines    basi  schen Kondensationsmittels mit einer Verbin  dung der Formel     II    umzusetzen.  



  Der auf diese Weise erhaltene     2-Oxy-4-          amino-        phenyl-ss-        diäthylamino-äthyl-thioäther     bildet ein     Reineke-Salz,    welches bei 175   schmilzt.  



  <I>Beispiel:</I>  3,6 g Natrium werden in 300     cm3        abs.          Äthanol    gelöst. Die Lösung wird mit<B>22g</B>       2-Oxy-4-amino-thiophenol    versetzt und unter       Rühren    21g     ss-Diäthylamino-äthylchlorid    zu  gefügt. Man kocht 1/2 Stunde     Rückfluss,    ver  dampft dann zur Trockne, nimmt in Chloro  form auf und wäscht mit Wasser. Nach dem  Trocknen der     Chloroformlösung    wird ver  dampft, wobei man 35 g     2-Oxy-4-amino-phenyl-          ,B-diäthylamino-äthyl-thioäther        gewinnt.     



  Die Verbindung bildet ein     Reineke-Salz,     welches nach     Umkristallisieren        aus    Äthanol  Wasser bei 175  schmilzt.



  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-oxy-4-aminophenyl-ß-diethylamino-ethy 1-thioether.



  This thioether has a strong inhibitory effect on bacterial growth, on the growth of fungi as well as a certain vermicidal effect and is said to be used as a chemotherapeutic and antimycotic.



  The process according to the invention for preparing the new aromatic thioether is characterized in that 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 metal salt of 2-oxy-4-aminothiophenol (X = Me, e.g. sodium, potassium, etc.) can be treated with a compound of the formula II in which Y is a halogen atom or another easily cleaving remainder, such as. B. alkyl or aryl sulfonyloxy, means. It is also possible to implement the 2-oxy-4-aminothiophenol in the presence of a basic condensing agent with a connec tion of the formula II.



  The 2-oxy-4-aminophenyl-ss-diethylamino-ethyl-thioether obtained in this way forms a Reineke salt which melts at 175.



  <I> Example: </I> 3.6 g sodium are in 300 cm3 abs. Dissolved ethanol. The solution is mixed with <B> 22g </B> 2-oxy-4-aminothiophenol and added with stirring 21g of ß-diethylaminoethyl chloride. The mixture is refluxed for 1/2 hour, then evaporated to dryness, taken up in chloro form and washed with water. After the chloroform solution has dried, the mixture is evaporated, 35 g of 2-oxy-4-aminophenyl, B-diethylamino-ethyl-thioether being obtained.



  The compound forms a Reineke salt, which melts at 175 after recrystallization from ethanol-water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines neuen aro matischen Thioäthers, dadurch gekennzeich- net, dass man auf eine Verbindung der Formel EMI0001.0049 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 refers to a compound of the formula EMI0001.0049 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-Oxy-4-amino-phenyl- ss-diäthylamino-äthyl-thioäther bildet ein Reineke-Salz, welches bei 175 schmilzt. Der neue Thioäther soll als Chemothera- peuticum und Antimycoticum Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man eine Verbindung der Formel I mit einem ss-Diäthylamino-äthyl- halogenid umsetzt. The 2-oxy-4-aminophenyl-ß-diethylamino-ethyl-thioether obtained in this way forms a Reineke salt which melts at 175. The new thioether is said to be used as a chemotherapeutic and antimycotic. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that a compound of the formula I is reacted with an β-diethylamino-ethyl halide.
CH301702D 1951-11-16 1951-11-16 Process for the preparation of a new aromatic thioether. CH301702A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH297993T 1951-11-16
CH301702T 1951-11-16

Publications (1)

Publication Number Publication Date
CH301702A true CH301702A (en) 1954-09-15

Family

ID=25733937

Family Applications (1)

Application Number Title Priority Date Filing Date
CH301702D CH301702A (en) 1951-11-16 1951-11-16 Process for the preparation of a new aromatic thioether.

Country Status (1)

Country Link
CH (1) CH301702A (en)

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