CH237127A - Process for the preparation of 4-amino-benzenesulfondodecanoylamide. - Google Patents

Process for the preparation of 4-amino-benzenesulfondodecanoylamide.

Info

Publication number
CH237127A
CH237127A CH237127DA CH237127A CH 237127 A CH237127 A CH 237127A CH 237127D A CH237127D A CH 237127DA CH 237127 A CH237127 A CH 237127A
Authority
CH
Switzerland
Prior art keywords
amino
preparation
benzenesulfondodecanoylamide
group
solution
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Schering
Original Assignee
Ag Schering
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 Ag Schering filed Critical Ag Schering
Publication of CH237127A publication Critical patent/CH237127A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Terfahren    zur Herstellung von     4-Amino-benzolsulfondodelianoylamid.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur     Herstellung    von     4-Amino-          benzolsulfondodekanoylamid,    das dadurch ge  kennzeichnet ist, dass man ein     Benzolsulfon-          dodekanoylamid,    das in     4-Stellung    zur     Sul-          fondodekanoylamidgruppe    eine durch Reduk  tion in die     Aminogruppe        überführbare    Gruppe  enthält, mit einem reduzierenden Mittel be  handelt.  



  Solche in die     Aminogruppe        überführbare     Gruppen sind die     Nitro-,        Nitroso-,        Azo-,          Hydrazo-,        Azoxy-,        Benzylamino-,        Carbo-          benzyloxyamino-    und dergleichen Gruppen.

    <I>Beispiel:</I>  20,2 g     4-Nitro-benzolsulfonamid    werden  in 250     cm@        Pyridin    gelöst und zu der Lösung  bei einer     Temperatur    von 20 bis     ä0     unter  Rühren allmählich 21,9 g     Dodekanoylchlorid     zugegeben. Nach völligem     Eintragen    wird  die Lösung eine Stunde auf 70 bis 80  er  wärmt, dann abgekühlt und in verdünnte  Salzsäure eingerührt. Der entstandene Nie-         derschlag    wird abgesaugt, mit Wasser aus  gewaschen, zwecks Reinigung in verdünnter       Natriumkarbonatlösung    aufgenommen, die  Lösung mit Tierkohle behandelt, abgesaugt  und das Filtrat angesäuert.

   Das auf diese  Weise erhaltene Nitroprodukt wird in  5 %     igem    Ammoniak gelöst und Schwefelwas  serstoff bis zur Sättigung eingeleitet. Die  zur Trockne     eingeengte    Lösung wird mit  Wasser aufgenommen und das     4-Amino-          benzolsulfondodekanoylamid    durch Zusatz  von Essigsäure gefällt.     Smp.    127 bis 129,5   (aus 80%igem Alkohol).  



  Die Verbindung ist identisch mit der  jenigen des     schweiz.    Patentes Nr. 222969  und kann ebenfalls als Arzneimittel sowie  als Zwischenprodukt zur Herstellung von       Arzneimitteln    und andern technisch wert  vollen Substanzen     Verwendung    finden.



      The process for the preparation of 4-amino-benzenesulfondodelianoylamide. The present patent relates to a process for the preparation of 4-amino benzenesulfondodecanoylamide, which is characterized in that a benzenesulfonododecanoylamide which contains a group which can be converted into the amino group by reduction in the 4-position to the sulfondodecanoylamide group a reducing agent treats.



  Such groups which can be converted into the amino group are the nitro, nitroso, azo, hydrazo, azoxy, benzylamino, carbobenzyloxyamino and the like groups.

    <I> Example: </I> 20.2 g of 4-nitro-benzenesulfonamide are dissolved in 250 cm @ pyridine and 21.9 g of dodecanoyl chloride are gradually added to the solution at a temperature of 20 to -0 with stirring. After complete entry, the solution is heated to 70 to 80 for one hour, then cooled and stirred into dilute hydrochloric acid. The resulting precipitate is suctioned off, washed out with water, taken up in dilute sodium carbonate solution for cleaning purposes, the solution treated with animal charcoal, suctioned off and the filtrate acidified.

   The nitro product obtained in this way is dissolved in 5% ammonia and hydrogen sulfide is passed in until it is saturated. The solution, which has been concentrated to dryness, is taken up with water and the 4-aminobenzenesulfondodecanoylamide is precipitated by adding acetic acid. M.p. 127 to 129.5 (from 80% alcohol).



  The connection is identical to that of Switzerland. Patent No. 222969 and can also be used as a drug and as an intermediate product for the production of drugs and other technically valuable substances.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 4-Amino- benzolsulfondodekanoylamid, dadurch ge- kennzeichnet, dass man ein Benzolsulfon- dodeka.noylamid, das in 4-Stellung zur Sul- fondodekanoylamidbruppe eine durch Reduk tion in die Aminogruppe überführbare Gruppe enthält, mit einem reduzierenden Mittel behandelt. Die Verbindung schmilzt, aus 80 % igem Alkohol umkristallisiert, bei<B>127</B> bis 129,5 . PATENT CLAIM: Process for the production of 4-aminobenzenesulfondodecanoylamide, characterized in that a benzenesulfonododecanoylamide which contains a group which can be converted into the amino group by reduction in the 4-position to the sulfondodecanoylamide group is used with a reducing agent treated. The compound melts, recrystallized from 80% alcohol, at <B> 127 </B> to 129.5.
CH237127D 1938-02-02 1939-01-19 Process for the preparation of 4-amino-benzenesulfondodecanoylamide. CH237127A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE237127X 1938-02-02
CH231060T 1939-01-19

Publications (1)

Publication Number Publication Date
CH237127A true CH237127A (en) 1945-03-31

Family

ID=25727528

Family Applications (1)

Application Number Title Priority Date Filing Date
CH237127D CH237127A (en) 1938-02-02 1939-01-19 Process for the preparation of 4-amino-benzenesulfondodecanoylamide.

Country Status (1)

Country Link
CH (1) CH237127A (en)

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