CH230448A - Process for the preparation of a new ester of the oxy-stilbene series. - Google Patents

Process for the preparation of a new ester of the oxy-stilbene series.

Info

Publication number
CH230448A
CH230448A CH230448DA CH230448A CH 230448 A CH230448 A CH 230448A CH 230448D A CH230448D A CH 230448DA CH 230448 A CH230448 A CH 230448A
Authority
CH
Switzerland
Prior art keywords
preparation
dioxystilbene
oxy
new ester
diethyl
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH230448A publication Critical patent/CH230448A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/78—Benzoic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
    • C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
    • C07C39/215—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring containing, e.g. diethylstilbestrol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
    • C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
    • C07C69/28—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with dihydroxylic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids

Landscapes

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

Description

  

      Verfahren    zur Darstellung eines neuen     Esters    der     Ogy-stilbenreihe.       Es wurde gefunden, dass man zu einem  neuen Ester gelangen kann, wenn man     a,a'-          Diäthyl-4,4'-dioxystilben    durch Behandlung  mit einem     benzoylierenden    Mittel in den ent  sprechenden Monoester überführt.  



  Geeignete     benzoylierende    Mittel sind zum  Beispiel die     Benzoesäure    selbst, ihre Halo  genide oder Ester mit niederen Alkoholen       (Umesterung)    sowie auch ihr     Anhydrid.     



  Die neue Verbindung, das     a,a'-Diäthyl-          4,4'-dioxystilben-monobenzoat,    bildet farblose  Kristalle. Sie zeigt gegenüber den bekannten  hormonal wirksamen Verbindungen ohne       Steroidcharakter    eine     protrahiertere        Wirkung     im     O.estrus-    und     Uteruswae'hstumGtest    und soll  deshalb therapeutische Verwendung finden.

    <I>Beispiel:</I>  Eine Lösung von 4,4     Teilen        a,a'-Diäthyl-          4,4'-dioxystilben    und 3,6 Teilen     Benzoesäure-          anhydrid    in 50 Teilen trockenem     Pyridin     wird 2 Stunden unter     Rückfluss    gekocht. Das       Pyridin    wird hierauf im Vakuum abdestil-         liert    und der Rückstand in Äther aufgenom  men. Dabei scheidet sich das in Äther schwer  lösliche     Dibenzoat    des     a,a'-Diätliyl-4,4'-di-          oxystilben    fast quantitativ aus.

   Es     wird    ab  gesaugt und mehrmals in Äther gewaschen.  Die Ätherlösung wird mit verdünnter Schwe  felsäure, dann mit     verdünnter        Sodalösung,          und    schliesslich mit Wasser gewaschen, ge  trocknet und eingedampft. Der ölige Äther  rückstand wird in Methanol aufgenommen  und die     Methanollösung    mit Wasser bis zur  leichten     Trübung    versetzt. Über Nacht kri  stallisiert das     Monobenzoat,    das, aus Metha  nol umkristallisiert, farblose     Kristalle    bildet.



      Process for the preparation of a new ester of the Ogy stilbene series. It has been found that a new ester can be obtained if a, a'-diethyl-4,4'-dioxystilbene is converted into the corresponding monoester by treatment with a benzoylating agent.



  Suitable benzoylating agents are, for example, benzoic acid itself, its halides or esters with lower alcohols (transesterification) and also its anhydride.



  The new compound, the a, a'-diethyl 4,4'-dioxystilbene-monobenzoate, forms colorless crystals. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterine cavity test and should therefore be used therapeutically.

    <I> Example: </I> A solution of 4.4 parts of a, a'-diethyl-4,4'-dioxystilbene and 3.6 parts of benzoic anhydride in 50 parts of dry pyridine is refluxed for 2 hours. The pyridine is then distilled off in vacuo and the residue is taken up in ether. The dibenzoate of a, a'-dietliyl-4,4'-dioxystilbene, which is sparingly soluble in ether, is eliminated almost quantitatively.

   It is sucked off and washed several times in ether. The ether solution is washed with dilute sulfuric acid, then with dilute soda solution, and finally with water, dried and evaporated. The oily ether residue is taken up in methanol and water is added to the methanol solution until it becomes slightly cloudy. The monobenzoate crystallizes overnight and, when recrystallized from methanol, forms colorless crystals.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines neuen Esters, dadurch gekennzeichnet, dass man a,ä -Diäthyl-4,4'-dioxystilben durch Behand lung mit einem benzoylierenden Mittel in den entsprechenden Monoester überführt. Die neue Verbindung, das a,a'-Diäthyl- 4,4'-dioxystilben-mono-benzoat, bildet farb- lose Kristalle. PATENT CLAIM: Process for the preparation of a new ester, characterized in that a, ä-diethyl-4,4'-dioxystilbene is converted into the corresponding monoester by treatment with a benzoylating agent. The new compound, the a, a'-diethyl 4,4'-dioxystilbene-mono-benzoate, forms colorless crystals. Sie zeigt gegenüber den be kannten hormonal wirksamen Verbindungen ohne Steroidcharakter eine protrahiertere Wirkung im Oestrus- und Uteruswachstums- test und soll deshalb therapeutische Verwen dung finden. UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als benzoylieren- des Mittel Benzoesäureanhydrid verwendet wird. ?. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass als benzoylieren- des Mittel ein Benzoesäurehalogenid verwen det wird. Compared to the known hormonally active compounds without steroid character, it shows a more protracted effect in the oestrus and uterus growth test and should therefore find therapeutic use. SUB-CLAIMS: 1. Method according to claim, characterized in that benzoic anhydride is used as the benzoylating agent. ?. Method according to claim, characterized in that a benzoic acid halide is used as the benzoylating agent.
CH230448D 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series. CH230448A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH230448T 1938-07-02
CH225257T 1938-07-02

Publications (1)

Publication Number Publication Date
CH230448A true CH230448A (en) 1943-12-31

Family

ID=25726841

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230448D CH230448A (en) 1938-07-02 1938-07-02 Process for the preparation of a new ester of the oxy-stilbene series.

Country Status (1)

Country Link
CH (1) CH230448A (en)

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