CH235769A - Process for the preparation of 4-amino-benzenesulfonacetamide. - Google Patents

Process for the preparation of 4-amino-benzenesulfonacetamide.

Info

Publication number
CH235769A
CH235769A CH235769DA CH235769A CH 235769 A CH235769 A CH 235769A CH 235769D A CH235769D A CH 235769DA CH 235769 A CH235769 A CH 235769A
Authority
CH
Switzerland
Prior art keywords
amino
benzenesulfonacetamide
preparation
acid
converted
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 CH235769A publication Critical patent/CH235769A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • 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

Landscapes

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

Description

  

  Verfahren zur Herstellung von     4-Amino-benzolsulfonacetamid.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur.     Herstellung    von     4-Amino-          benzolsul.fonacetamid,    das dadurch gekenn  zeichnet ist, dass man ein     Benzolsulfenacet-          amid,    welches in     4-Stellung    eine durch Hy  drolyse in die     Aminogruppe        überführbare     Gruppe enthält,

   mittels eines oxydierenden  Mittels     in    die entsprechende     Sulfonverbin-          dung    überführt und diese darauf mit einem       hydrolisierenden    Mittel behandelt.  



  Die Verbindung ist bekannt und soll als  Arzneimittel     und    als     Zwischenprodukt        Ver-          Wendung    finden.  



  <I>Beispiel:</I>  23,2 g     4-Carbäthoxyamino-phenylschwe-          felchlorid    vom F = 68  (erhalten durch Re  duktion von     4-Carbäthoxyamino-phenylsul-          finsäurechlorid    mit Eisen und Salzsäure)  werden mit 5,9 g     Acetamid    in. 50 cm'     trok-          kenem        Pyridin    2 Stunden auf dem Wasser  bad erhitzt.

   Die Lösung wird dann unter  Kühlung mit verdünnter Salzsäure bis zur  kongosauren Reaktion versetzt und das aus  gefällte 4 -     Carbäthoxyamino    -     phenylsulfen-          säureacetamid    abgesaugt und ausgewaschen:  12,7 g der     Carbäthoxysulfenverbindung       werden     in    50%iger Essigsäure mit 3 %     iger          Kaliumpermanganatlösüng    bei Wasserbad  temperatur oxydiert. Das 4 -     Carbäthoxy-          amino-phenylsulfonsäure-acetylamid    scheidet  sich in reinem Zustande vom F=244' ab.  



  14,3 g der     Carbäthoxyverbindung    wer  den zur     Verseifung    der     Carbäthoxygruppe     mit 100 cm' doppelt normaler Natronlauge  bis zur Säurelöslichkeit     einer    Probe auf 80   erhitzt. Nach Abkühlung der Lösung     wird     mit Essigsäure angesäuert     und    das ausgefal  lene     4-Amino-phenylsulfonsäureacetamid    aus  Wasser     umkristallisiert.   <B>F=181</B> bis 182 .



  Process for the preparation of 4-amino-benzenesulfonacetamide. The present patent is a method for. Production of 4-amino-benzenesulphonacetamide, which is characterized in that a benzenesulfenacetamide which contains in the 4-position a group which can be converted into the amino group by hydrolysis,

   converted into the corresponding sulfone compound by means of an oxidizing agent and then treated with a hydrolyzing agent.



  The compound is known and is thought to find use as a medicinal product and as an intermediate.



  <I> Example: </I> 23.2 g of 4-carbethoxyamino-phenylsulphur chloride of F = 68 (obtained by reducing 4-carbethoxyamino-phenylsulphic acid chloride with iron and hydrochloric acid) are mixed with 5.9 g of acetamide in 50 cm 'of dry pyridine heated on the water bath for 2 hours.

   The solution is then admixed with dilute hydrochloric acid while cooling until it reacts in the Congo and the precipitated 4-carbethoxyamino-phenylsulfenic acid acetamide is suctioned off and washed out: 12.7 g of the carbethoxysulfen compound are oxidized in 50% acetic acid with 3% potassium permanganate solution in a water bath . The 4-carbethoxyamino-phenylsulfonic acid acetylamide separates in the pure state from the F = 244 '.



  14.3 g of the carbethoxy compound who is heated to the saponification of the carbethoxy group with 100 cm 'double normal sodium hydroxide solution until a sample is acid-soluble. After cooling the solution, it is acidified with acetic acid and the precipitated 4-aminophenylsulfonic acid acetamide is recrystallized from water. <B> F = 181 </B> to 182.

Claims (1)

UNTERANSPRUCH: Verfahren zur Herstellung von 4-Amino- benzolsulfonacetamid, dadurch gekennzeich net, dass man ein Benzolsulfenacetamid, wel ches in 4-Stellung eine durch Hydrolyse in die Aminogruppe überführbare Gruppe ent hält, mittels eines Oxydationsmittels in die entsprechende Sulfonverbindung überführt und diese darauf mit einem hydrolysierenden Mittel behandelt. ' SUBSTANTIAL CLAIM: A process for the production of 4-Amino-benzenesulfonacetamide, characterized in that a benzenesulfenacetamide, which in the 4-position contains a group that can be converted into the amino group by hydrolysis, is converted into the corresponding sulfone compound by means of an oxidizing agent and then with it treated with a hydrolyzing agent. '
CH235769D 1941-01-22 1942-01-21 Process for the preparation of 4-amino-benzenesulfonacetamide. CH235769A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE235769X 1941-01-22

Publications (1)

Publication Number Publication Date
CH235769A true CH235769A (en) 1944-12-31

Family

ID=5898518

Family Applications (1)

Application Number Title Priority Date Filing Date
CH235769D CH235769A (en) 1941-01-22 1942-01-21 Process for the preparation of 4-amino-benzenesulfonacetamide.

Country Status (1)

Country Link
CH (1) CH235769A (en)

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