CH204380A - Process for preparing an aminobenzenesulfonic acid amide compound. - Google Patents

Process for preparing an aminobenzenesulfonic acid amide compound.

Info

Publication number
CH204380A
CH204380A CH204380DA CH204380A CH 204380 A CH204380 A CH 204380A CH 204380D A CH204380D A CH 204380DA CH 204380 A CH204380 A CH 204380A
Authority
CH
Switzerland
Prior art keywords
acid amide
sulfonic acid
ammonia
preparing
amide compound
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH204380A publication Critical patent/CH204380A/en

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Classifications

    • 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
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring

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

Description

  

  Verfahren zur Darstellung einer     Aminobenzolsulfonsäureamidverbindung.       Gemäss Angaben des schweizerischen Pa  tentes Nr. 199315 sind gewisse     Aminoacyl.     und     Oxyacylaminobenzol    -     sulfonsäureamide,     sowie deren     Substitutionsprodukte    durch ihre  Wirkung gegen bakterielle Infektionskrank  heiten ausgezeichnet.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung von     Amino-          acetylaminobenzol-4-sulfonsäureamid,    welches  dadurch gekennzeichnet ist, dass man auf ein       Acetylaminobenzol-4-sulfonsäureamid,    das im       Acetylrest    durch einen gegen Ammoniak aus  tauschbaren     Substituenten    substituiert ist,  Ammoniak zur Einwirkung bringt.

       Acetyl-          aminobenzol-4.sulfonsäureamide    mit     austausch.     fähigem     Substituenten    im     Acetylrest    sind vor  allem     Halogenacetylaminobenzol    - 4 -     sulfon-          säureamide,    im besonderen     Chloracetylamino-          benzol-4-sulfonsäureamid.    Ammoniak kann  man in wässeriger Lösung oder auch in rei  ner flüssiger Form zur Anwendung bringen.

    Das so erhältliche Aminoaoetylaminobenzol-         4-sulfonsäureamid    bildet farblose Kristalle  vom Schmelzpunkt 217  .     Mit    Salzsäure bil  det es ein Hydrochlorid, das aus verdünntem  Alkohol umkristallisiert den Schmelzpunkt  287   hat. Die neue     Verbindung    soll thera  peutische Anwendung finden.  



  <I>Beispiel:</I>  41,7g Hydrochlorid des     4-Aminobenzol-          sulfonsäureamids    werden in 400 cm' Wasser  gelöst und durch     portionaweise    Zugabe von  30 g     Chloracetylchlorid    und festem Natrium  acetat in das     Chloracetylaminobenzol-4-sul-          fonsäureamid    umgewandelt. Dieses kristalli  siert aus Methanol in farblosen Nadeln vom  Schmelzpunkt 212  . Durch Behandeln mit  wässerigem Ammoniak oder besser mit flüssi  gem Ammoniak erhält man daraus das     Amino-          aoetylamino@benzol-4-sulfonsäureamid,    das bei  217   schmilzt.

   Das Hydrochlorid, aus ver  dünntem Alkohol umkristallisiert, hat einen  Schmelzpunkt von 287  .



  Process for preparing an aminobenzenesulfonic acid amide compound. According to the Swiss patent no. 199315, certain are aminoacyl. and oxyacylaminobenzene - sulfonic acid amides, as well as their substitution products, are distinguished by their action against bacterial infectious diseases.



  The present patent relates to a process for the preparation of aminoacetylaminobenzene-4-sulfonic acid amide, which is characterized in that ammonia is brought into action on an acetylaminobenzene-4-sulfonic acid amide, which is substituted in the acetyl radical by a substituent that can be exchanged for ammonia .

       Acetyl aminobenzene-4.sulfonic acid amide with exchange. Above all, suitable substituents in the acetyl radical are haloacetylaminobenzene-4-sulfonic acid amides, in particular chloroacetylamino-benzene-4-sulfonic acid amide. Ammonia can be used in an aqueous solution or in pure liquid form.

    The amino aetylaminobenzene-4-sulfonic acid amide thus obtainable forms colorless crystals with a melting point of 217. With hydrochloric acid, it forms a hydrochloride that, recrystallized from dilute alcohol, has a melting point of 287. The new connection is intended to be used therapeutically.



  <I> Example: </I> 41.7 g of 4-aminobenzenesulfonic acid amide hydrochloride are dissolved in 400 cm 'of water and converted into chloroacetylaminobenzene-4-sulfonic acid amide by adding 30 g of chloroacetyl chloride and solid sodium acetate in portions. This crystallizes from methanol in colorless needles with a melting point of 212. By treatment with aqueous ammonia or, better, with liquid ammonia, the amino aoetylamino @ benzene-4-sulfonic acid amide, which melts at 217, is obtained therefrom.

   The hydrochloride, recrystallized from dilute alcohol, has a melting point of 287.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer Amino- benzolsulfonsäureamidverbindung,dadurch ge kennzeichnet, dass man auf ein Acetylamino- benzol-4-sulfonsäureamid, das im Acetylrest durch einen gegen Ammoniak austauschbaren Substituenten substituiert ist, Ammoniak zur Einwirkung bringt. Das so erhältliche Aminoacetylaminobeii- zol-4-sulfonsäureamid bildet farblose Kristalle vom Schmelzpunkt 217 , mit Salzsäure bil det es ein Hydrochlorid, das aus verdünntem Alkohol umkristallisiert, den Schmelzpunkt 287<B>0</B> hat. PATENT CLAIM: Process for the production of an aminobenzenesulfonic acid amide compound, characterized in that ammonia is brought into action on an acetylamino-benzene-4-sulfonic acid amide, which is substituted in the acetyl radical by a substituent which can be replaced by ammonia. The aminoacetylaminobeiizole-4-sulfonic acid amide thus obtainable forms colorless crystals with a melting point of 217; with hydrochloric acid, it forms a hydrochloride that recrystallizes from dilute alcohol and has a melting point of 287. UN TERAN SPRüCHE 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass ein Halogenacetyl- amiriobenzol-4-sulfonsäureamid für die Um setzung -verwendet wird. 2. Verfahren nach Patentanspruch und Unter anspruch 1, dadurch gekennzeichnet, dass Chloracetylaminobenzol-4-sulfonsäureamid verwendet wird. 3. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass flüssiges Ammoniak für die Umsetzung verwendet wird. UN TERAN PROPOSALS 1. Process according to claim, characterized in that a halogen acetyl amiriobenzene-4-sulfonic acid amide is used for the implementation. 2. The method according to claim and sub-claim 1, characterized in that chloroacetylaminobenzene-4-sulfonic acid amide is used. 3. The method according to claim, characterized in that liquid ammonia is used for the reaction.
CH204380D 1936-02-06 1937-01-12 Process for preparing an aminobenzenesulfonic acid amide compound. CH204380A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE204380X 1936-02-06

Publications (1)

Publication Number Publication Date
CH204380A true CH204380A (en) 1939-04-30

Family

ID=5781523

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204380D CH204380A (en) 1936-02-06 1937-01-12 Process for preparing an aminobenzenesulfonic acid amide compound.

Country Status (1)

Country Link
CH (1) CH204380A (en)

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