CH193919A - Process for the preparation of 3-acetoxy-17-chloro-androstene. - Google Patents

Process for the preparation of 3-acetoxy-17-chloro-androstene.

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Publication number
CH193919A
CH193919A CH193919DA CH193919A CH 193919 A CH193919 A CH 193919A CH 193919D A CH193919D A CH 193919DA CH 193919 A CH193919 A CH 193919A
Authority
CH
Switzerland
Prior art keywords
preparation
chloro
acetoxy
androstene
agent
Prior art date
Application number
Other languages
German (de)
Inventor
Schering-Kahlbaum A G
Original Assignee
Schering Kahlbaum 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 Schering Kahlbaum Ag filed Critical Schering Kahlbaum Ag
Publication of CH193919A publication Critical patent/CH193919A/en

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

Description

  

  Verfahren zur Darstellung von     3-Acetogy-17-chlor-androsten.       Die vorliegende Erfindung     betrifft    ein Ver  fahren zur Darstellung von     3-Acetoxy-17-          chlor-androsten,    welches dadurch     gekenn-          zeichnetist,        dass    man     Androstendiol-3,17-mono-          acetat-3    der Einwirkung eines Mittels unter  wirft, das eine     Hydroxylgruppe    durch Chlor  zu ersetzen vermag.  



  Geeignete Mittel hierfür sind z. B. Phos  phorchloride,     Thionylchlorid    und andere Chlor  verbindungen, die neben dem austauschfähigen  Chloratom ein Element oder eine Atomgruppe  enthalten, welche     Sauerstoff    oder     Hydroxyl     zu binden vermag. Vorteilhaft nimmt man  die     Chlorierung    in einem Lösungsmittel vor,  welches vom     Ohlorierungsmittel    nicht ange  griffen wird.  



  Die neue Verbindung soll als Ausgangs  material für die Darstellung physiologisch  wertvoller Verbindungen Verwendung finden.  <I>Beispiel:</I>  1,1 g     Androstendiol-3,17-monoacetat-3     werden in 5     oms    trockenem     Tetrachlorkohlen-          stoff    gelöst. Zur Lösung werden unter Eis  kühlung 0,7 g     Phosphorpentachlorid    hinzu  getan. Die Reaktionsmischung lässt man unter    mehrfachem     Umschütteln    bei Zimmertempe  ratur stehen.

   Nach Verlauf von etwa 12  Stunden giesst man die klare Lösung in Eis  wasser und     äthert    aus.     Sodänn    wird die  ätherische Lösung mit     Sodalösung    und Wasser  gewaschen und nach Trocknung verdampft.  Den so erhaltenen Rückstand kristallisiert  man aus einem Gemisch von     Aceton-Methanol     um, wobei man das     3-Aeetoxy-17-chlor-an-          drosten    vom Schmelzpunkt 170 0 in einer       Ausbeute        von        ca.60-70%        der        Theorie        er-          hält.  



  Process for the preparation of 3-acetogy-17-chloro-androstene. The present invention relates to a method for the preparation of 3-acetoxy-17-chloro-androstene, which is characterized in that androstenediol-3,17-monoacetate-3 is subjected to the action of an agent which has a hydroxyl group Able to replace chlorine.



  Suitable means for this are, for. B. Phos phorchloride, thionyl chloride and other chlorine compounds that contain an element or a group of atoms in addition to the exchangeable chlorine atom, which is able to bind oxygen or hydroxyl. The chlorination is advantageously carried out in a solvent which is not attacked by the chlorinating agent.



  The new compound is to be used as a starting material for the preparation of physiologically valuable compounds. <I> Example: </I> 1.1 g androstenediol-3,17-monoacetate-3 are dissolved in 5 oms of dry carbon tetrachloride. 0.7 g of phosphorus pentachloride are added to the solution while cooling with ice. The reaction mixture is left to stand at room temperature with repeated shaking.

   After about 12 hours, the clear solution is poured into ice water and etherified. The ethereal solution is washed with soda solution and water and evaporated after drying. The residue obtained in this way is recrystallized from a mixture of acetone-methanol, the 3-ethoxy-17-chloro-anode having a melting point of 170 ° in a yield of about 60-70% of theory.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 3-Acetoxy- 17-chlorandrosten, dadurch gekennzeichnet, dass man Androstendiol-3,17-monoacetat-3 der Einwirkung eines Mittels unterwirft, das eine Hydroxylgruppe durch Chlor zu ersetzen ver mag. Die neue Verbindung schmilzt bei<B>170'.</B> UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man Phosphorpentachlorid als Chlorierungsmittel verwendet. PATENT CLAIM: A process for the preparation of 3-acetoxy-17-chlorandrostene, characterized in that androstenediol-3,17-monoacetate-3 is subjected to the action of an agent which may replace a hydroxyl group with chlorine. The new compound melts at <B> 170 '. </B> SUBClaim: Process according to patent claim, characterized in that phosphorus pentachloride is used as the chlorinating agent.
CH193919D 1935-01-29 1936-01-27 Process for the preparation of 3-acetoxy-17-chloro-androstene. CH193919A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE193919X 1935-01-29

Publications (1)

Publication Number Publication Date
CH193919A true CH193919A (en) 1937-11-15

Family

ID=5741634

Family Applications (1)

Application Number Title Priority Date Filing Date
CH193919D CH193919A (en) 1935-01-29 1936-01-27 Process for the preparation of 3-acetoxy-17-chloro-androstene.

Country Status (1)

Country Link
CH (1) CH193919A (en)

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