CH206629A - Process for preparing an aminobenzenesulfonic acid amide compound. - Google Patents

Process for preparing an aminobenzenesulfonic acid amide compound.

Info

Publication number
CH206629A
CH206629A CH206629DA CH206629A CH 206629 A CH206629 A CH 206629A CH 206629D A CH206629D A CH 206629DA CH 206629 A CH206629 A CH 206629A
Authority
CH
Switzerland
Prior art keywords
acid amide
benzene
preparing
amide compound
sulfonic acid
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 CH206629A publication Critical patent/CH206629A/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     schweiz.    Patentes  199315 sind gewisse     Aminoacyl-    und     O$y-          acyl-aminobenzolsulfonsäureamide    sowie deren       Substitutionsprodukte    durch ihre Wirkung  gegen bakterielle Infektionskrankheiten aus  gezeichnet.  



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung von     Butyl-          aminoacetylamino        -benzol-4-sulfonsäureamid,     welches dadurch gekennzeichnet ist, dass man  auf ein     Acetylamino-benzol-4-sulforisäureamid,     das in der     Acetylgruppe    durch einen gegen  einen     Aminrest    austauschfähigen     Substituen-          ten    substituiert ist,     Butylamin    einwirken lässt.

         Vorzugsweise    finden     Halogenacetylamino-          benzol-4-sulfonsäureamide,    im besonderen       Chloracetylamino-benzol-4-        sulfonsäureamid,     Verwendung. Die Reaktion erfolgt zweck  mässig in alkoholischer Lösung unter Erwär  men. Das so erhältliche     Butylaminoacetyl-          amino-benzol-4-sulfonsäureamid    bildet farblose  Kristalle vom Schmelzpunkt<B>1671.</B> Es soll  therapeutische Anwendung finden.

      <I>Beispiel:</I>  41,7 g Hydrochlorid des     4-Aminobeiizol-          sulfonsäureamids    werden in 400 cm,' Wasser  gelöst und durch     portionsweise    Zugabe von  30 g     Chloräcetylchlorid    und festem Natrium  acetat in das     @Chloracetylamino-bei)zol-4-sul-          fonsäureamid    umgewandelt. Dieses kristalli  siert aus Methanol in farblosen Nadeln vom  Schmelzpunkt 2120.

   Durch Behandeln der       Chloracetylverbindung    mit     Butylamin    in sie  dendem Alkohol erhält man das     Butylamino-          acetylaminobenzol-4-sulfonsäureamid,    das nach       Umkristallisieren    aus Methylalkohol bei 167    schmilzt.



  Process for preparing an aminobenzenesulfonic acid amide compound. According to the Swiss. Patent 199315 are certain aminoacyl- and O $ y-acyl-aminobenzolsulfonsäureamide and their substitution products are distinguished by their action against bacterial infectious diseases.



  The subject of the present patent is a process for the preparation of butylaminoacetylamino-benzene-4-sulfonic acid amide, which is characterized in that an acetylamino-benzene-4-sulforic acid amide, which in the acetyl group is exchangeable for an amine residue, is used is substituted, butylamine can act.

         Haloacetylaminobenzene-4-sulfonic acid amides, in particular chloroacetylamino-benzene-4-sulfonic acid amide, are preferably used. The reaction is conveniently carried out in an alcoholic solution with heating. The butylaminoacetylamino-benzene-4-sulfonic acid amide obtainable in this way forms colorless crystals with a melting point of <B> 1671. </B> It is intended to be used therapeutically.

      <I> Example: </I> 41.7 g of 4-aminobeiizolesulfonic acid amide hydrochloride are dissolved in 400 cm of water and converted into the chloroacetylamino-azole-4 by adding 30 g of chloroacetyl chloride and solid sodium acetate in portions -sulphonic acid amide converted. This crystallizes from methanol in colorless needles with a melting point of 2120.

   Treatment of the chloroacetyl compound with butylamine in the alcohol gives the butylaminoacetylaminobenzene-4-sulfonic acid amide, which melts at 167 after recrystallization from methyl alcohol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer Amino- benzolsulfonsäureamid-Verbindung, dadurch gekennzeichnet, dass man auf ein Acetyl- amino-benzol-4-sulfonsäureamid, das in der Acetylgruppe durch einen gegen einen Amin rest austauschfähigen Substituenten substi tuiert ist, Butylamin einwirken lässt. Das so erhältliche Butylamirioacetylamirio- benzol-4-sulfonsäureamid bildet farblose Kri stalle vom Schmelzpunkt<B>1670.</B> UNTERANSPRüCHE 1. PATENT CLAIM: Process for the production of an aminobenzenesulfonic acid amide compound, characterized in that butylamine is allowed to act on an acetylamino-benzene-4-sulfonic acid amide which is substituted in the acetyl group by a substituent which can be exchanged for an amine residue. The butylamirioacetylamiriobenzene-4-sulfonic acid amide which can be obtained in this way forms colorless crystals with a melting point of <B> 1670. </B> SUBClaims 1. Verfahren nach Patentanspruch, dadurch g e 'kentizeichriet, dass ein Halogeriaeetyl- e amino-benzol-4-sulfotisäureamid Verwen dung findet. 2. Verfahren nach Patentanspruch und Unter anspruch 1, dadurch gekennzeichnet, dass Chloracetylamirio-benzol-4-sulforisäureamid Verwendung findet. 3. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Umsetzung in Gegenwart von Alkohol durchgeführt wird. 4. Process according to patent claim, characterized in that a halo-ethyl-e-amino-benzene-4-sulfotic acid amide is used. 2. The method according to claim and sub-claim 1, characterized in that chloroacetylamirio-benzene-4-sulforic acid amide is used. 3. The method according to claim, characterized in that the reaction is carried out in the presence of alcohol. 4th Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass die Reaktionsmischung erwärmt wird. Method according to claim, characterized in that the reaction mixture is heated.
CH206629D 1936-02-06 1937-01-12 Process for preparing an aminobenzenesulfonic acid amide compound. CH206629A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE206629X 1936-02-06
CH204380T 1937-01-12

Publications (1)

Publication Number Publication Date
CH206629A true CH206629A (en) 1939-08-15

Family

ID=25724047

Family Applications (1)

Application Number Title Priority Date Filing Date
CH206629D CH206629A (en) 1936-02-06 1937-01-12 Process for preparing an aminobenzenesulfonic acid amide compound.

Country Status (1)

Country Link
CH (1) CH206629A (en)

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