CH300418A - Process for the preparation of a new thioether. - Google Patents

Process for the preparation of a new thioether.

Info

Publication number
CH300418A
CH300418A CH300418DA CH300418A CH 300418 A CH300418 A CH 300418A CH 300418D A CH300418D A CH 300418DA CH 300418 A CH300418 A CH 300418A
Authority
CH
Switzerland
Prior art keywords
preparation
thioether
dimethylamino
phenyl
new thioether
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 CH300418A publication Critical patent/CH300418A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C07C319/24—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides by reactions involving the formation of sulfur-to-sulfur bonds
    • 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
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Description

  

  Verfahren     zur        Herstellung        eines    neuen     Thioäthers.       Es wurde gefunden, dass Verbindungen  der allgemeinen Formel  
EMI0001.0005     
    in welcher     R1    einen niederen     Alkylrest,    R2  einen niederen     Alkyl-    oder     Aralkylrest,    n die  Zahl 1, 2 oder 3 und m die Zahl 1, 2, 3 oder  4 bedeutet, sowie deren     quaternären    Salze  wertvolle therapeutische Eigenschaften auf  weisen.  



  So wirken Verbindungen dieser Formel       beispielsweise        analgetisch,    Bei einigen der  selben kann durch     Quaternisierung    des Stick  stoffatoms eine     Verstärkung    der Wirkung  erzielt werden.  



  Gegenstand des vorliegenden Patentes ist  nun ein Verfahren- zur Herstellung eines der  eingangs beschriebenen     Thioäther.    Das erfin  dungsgemässe Verfahren ist dadurch gekenn  zeichnet, dass man eine Verbindung der  Formel  
EMI0001.0016     
    mit. salpetriger Säure behandelt und auf den  entstandenen Alkohol ein     Acetylierungsmittel     einwirken lässt. Das so erhaltene     1-Dimethyl-          amino    - 3 -     phenyl    - 3 -     acetoxymethyl    - 5 -     methyl-          mercapto-pentan    bildet ein farbloses, unter  0,15 mm bei 135 bis 140  siedendes Öl. Es soll  therapeutische     Verwendung    finden.  



  <I>Beispiel:</I>  17,1 g     1-Dimethylamino-3-phenyl-3-amino-          methyl-5-methylmercapto-pentan    werden in  70     cm3        2n-Schwefelsäure    gelöst und unter  Kühlung und     Turbinieren    mit einer Lösung  von 5 g     Natriumnitrit    in 30     em3    Wasser ver  setzt. Nach     1/2        Stunde        alkalisiert    man mit  konzentrierter     Sodalösung    und schüttelt die       Oxymethylverbindung    mit Äther aus.

   Der  Auszug wird nach dem Trocknen     verdampft.     Der Rückstand wird in 20     em3        Pyridin    ge  löst und mit 10     cm3        Essigsäureanhydrid    ver  setzt.

   Man     turbiniert    23 Stunden bei 20 , ver  dampft dann im Vakuum bis zur öligen Kon  sistenz, versetzt     -mit    Wasser und macht mit       Pottaschelösung        alkalisch.    Nach dem Auszie  lien mit Äther und Trocknen desselben     destil-          Iiert    man im     Hochvakuum.    Man erhält 8 g       1-Dimethylamino    - 3 -     phenyl    - 3 -     acetoxymethyl-          5-methylmexcapto-pentan    als unter 0,15 mm  bei 135 bis 140  siedendes Öl.



  Process for the preparation of a new thioether. It was found that compounds of the general formula
EMI0001.0005
    in which R1 is a lower alkyl radical, R2 is a lower alkyl or aralkyl radical, n is the number 1, 2 or 3 and m is the number 1, 2, 3 or 4, and their quaternary salts have valuable therapeutic properties.



  For example, compounds of this formula have an analgesic effect. In some of them, the effect can be increased by quaternizing the nitrogen atom.



  The present patent now relates to a process for producing one of the thioethers described at the beginning. The process according to the invention is characterized in that a compound of the formula
EMI0001.0016
    With. treated with nitrous acid and an acetylating agent is allowed to act on the alcohol formed. The 1-dimethylamino-3-phenyl-3-acetoxymethyl-5-methyl-mercapto-pentane obtained in this way forms a colorless oil which boils at 135 to 140 under 0.15 mm. It should find therapeutic use.



  <I> Example: </I> 17.1 g of 1-dimethylamino-3-phenyl-3-aminomethyl-5-methylmercapto-pentane are dissolved in 70 cm3 of 2N sulfuric acid and, with cooling and turbination, with a solution of 5 g sodium nitrite in 30 cubic meters of water. After 1/2 hour, alkalize with concentrated soda solution and shake out the oxymethyl compound with ether.

   The extract is evaporated after drying. The residue is dissolved in 20 cubic meters of pyridine and 10 cm3 of acetic anhydride are added.

   Turbine is carried out for 23 hours at 20, then evaporated in vacuo to an oily consistency, mixed with water and made alkaline with potash solution. After stripping with ether and drying it, it is distilled in a high vacuum. 8 g of 1-dimethylamino-3-phenyl-3-acetoxymethyl-5-methylmexcapto-pentane are obtained as an oil boiling below 0.15 mm at 135 to 140.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen Thioäthers, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI0002.0001 mit salpetriger Säure behandelt und auf den entstandenen Alkohol ein Acetylierungsmittel einwirken lässt. Das so erhaltene 1-Dimethyl- amino - 3 - phenyl - 3 - acetoxymethyl - 5 - methy 1 mercapto-pentan bildet ein farbloses, unter 0,15 mm bei 135 bis 140 siedendes Öl. Es soll therapeutische Verwendung finden. PATENT CLAIM Process for the preparation of a new thioether, characterized in that a compound of the formula EMI0002.0001 Treated with nitrous acid and let an acetylating agent act on the alcohol formed. The 1-dimethylamino-3-phenyl-3-acetoxymethyl-5-methyl-mercapto-pentane obtained in this way forms a colorless oil which boils at 135 to 140 under 0.15 mm. It should find therapeutic use.
CH300418D 1951-07-26 1951-07-26 Process for the preparation of a new thioether. CH300418A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH300418T 1951-07-26

Publications (1)

Publication Number Publication Date
CH300418A true CH300418A (en) 1954-07-31

Family

ID=4490662

Family Applications (1)

Application Number Title Priority Date Filing Date
CH300418D CH300418A (en) 1951-07-26 1951-07-26 Process for the preparation of a new thioether.

Country Status (1)

Country Link
CH (1) CH300418A (en)

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