CH255624A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

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Publication number
CH255624A
CH255624A CH255624DA CH255624A CH 255624 A CH255624 A CH 255624A CH 255624D A CH255624D A CH 255624DA CH 255624 A CH255624 A CH 255624A
Authority
CH
Switzerland
Prior art keywords
reaction
aromatic
act
compound
dependent
Prior art date
Application number
Other languages
German (de)
Inventor
Ag J R Geigy
Original Assignee
Ag J R Geigy
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 J R Geigy filed Critical Ag J R Geigy
Publication of CH255624A publication Critical patent/CH255624A/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
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

       

  Verfahren zur Herstellung eines aromatischen     Acylsulfonamids.            Gegenstand    vorliegenden Patentes ist ein  Verfahren zur Herstellung eines aromatischen       Aevlsulfonamids.    Das Verfahren     ist    dadurch       gekennzeichnet,        da.ss    man eine Verbindung  der     Formel     
EMI0001.0008     
         #        au        f        eine        Verbindung        der        Formel     
EMI0001.0016     
    worin X und Y zwei reaktionsfähige,

   bei der  Reaktion mit Ausnahme einer in einem  von ihnen enthaltenen     NH-Gruppe    sich     ab-          paltende    Reste bedeuten, einwirken lässt.  



  Die entstandene neue     Verbindung,    das  N -     (f        '-        Naphthoyl)    - p -     toluolsulf        onamid,     schmilzt bei     166--168     und soll als Desinfek  tionsmittel', z. B. für Gebrauchsgegenstände,       V < ,rwendung    finden.  



       Beispiel        r:     17,1 Teile     p-Toluolsulfonamid    werden in  100 Teilen     Nitrobenzol    suspendiert und mit  19 Teilen Aluminiumchlorid und 19 Teilen       ss-Nnphthoesä,urechlorid    versetzt. Das Ge  misch wird 2 Stunden auf     50     erwärmt und  hierauf das     Lösungsmittel    mit     Wasserdampf          abdestilliert.    Der Rückstand wird in Soda  lösung aufgenommen, mit Tierkohle behan  delt und filtriert. Aus dem Filtrat wird das  N -     (f3    -     Naphthoyl)    - p -     toluolsulfonamid    mit.

      Essigsäure ausgefällt und durch     Umkristal-          lisieren    aus Alkohol gereinigt.  



  Statt     unter        Zuhilfenahme    eines     Konden-          sationsmittels    kann die Reaktion auch in  Gegenwart eines     säurebindenden        Mittels,    wie  z. B. von     Pyridin    oder     Dimethylanilin,    oder  in Gegenwart eines     Katalysators,    wie z. B.  von Kupferpulver,     ausgeführt    werden.  



  An Stelle eines,     Halogenids    kann auch die       freie        ss-Naphthoesäure    in Gegenwart eines       Kondensationsmittels,        wie        Phospharpentogyd     oder     Phosphorpentachlorid,    verwendet werden.  <I>Beispiel 2:</I>  28,6 Teile     ss-Naphthoesäureamid    werden  in 200 Teilen     absolutem        Xylol    gelöst. Dann  fügt man 8 Teile     Natriumamid    hinzu und  erwärmt bis zum Aufhören der Ammoniak  entwicklung.

   Nach dem Abkühlen gibt man  38 Teile     p-To.luolsulfochlorid    in<B>100</B> Teilen       Xylol    zu und erhitzt mehrere     Stunden    unter  Rückfloss. Nach     beendeter    Reaktion wird das       Xylol    im Vakuum     abdestilliert.    Der Rück  stand wird in     Bikarbona,tlösung    aufgenom  men, mit Tierkohle behandelt, filtriert und  durch Ansäuern     ausgefällt.    Das     N-(ss-Naph-          thGyl)-p-toluol'sulf        onamid    wird aus verdünn  tem Alkohol     umkristallisiert    und so völlig  rein erhalten.



  Process for the preparation of an aromatic acylsulfonamide. The present patent relates to a process for the preparation of an aromatic sulfonamide. The process is characterized in that a compound of the formula
EMI0001.0008
         # to a compound of the formula
EMI0001.0016
    where X and Y are two reactive,

   in the reaction, with the exception of an NH group contained in one of them, means splitting off radicals, can act.



  The resulting new compound, the N - (f '- naphthoyl) - p - toluenesulfonamide, melts at 166-168 and is said to be used as a disinfectant', e.g. B. for everyday objects, V <, find application.



       Example r: 17.1 parts of p-toluenesulfonamide are suspended in 100 parts of nitrobenzene, and 19 parts of aluminum chloride and 19 parts of ß-Nnphthoic acid chloride are added. The mixture is heated to 50 for 2 hours and the solvent is then distilled off with steam. The residue is taken up in soda solution, treated with animal charcoal and filtered. The N - (f3 - naphthoyl) - p - toluenesulfonamide is formed from the filtrate.

      Acetic acid precipitated and purified by recrystallization from alcohol.



  Instead of using a condensation agent, the reaction can also be carried out in the presence of an acid-binding agent, such as B. of pyridine or dimethylaniline, or in the presence of a catalyst, such as. B. of copper powder.



  Instead of a halide, it is also possible to use the free β-naphthoic acid in the presence of a condensing agent such as phospharpentogide or phosphorus pentachloride. Example 2: 28.6 parts of β-naphthoic acid amide are dissolved in 200 parts of absolute xylene. Then 8 parts of sodium amide are added and the mixture is heated until the evolution of ammonia ceases.

   After cooling, 38 parts of p-To.luolsulfochlorid in 100 parts of xylene are added and the mixture is heated under reflux for several hours. After the reaction has ended, the xylene is distilled off in vacuo. The residue is taken up in bicarbonate solution, treated with animal charcoal, filtered and precipitated by acidification. The N- (ss-NaphthGyl) -p-toluene sulfonamide is recrystallized from dilute alcohol and thus obtained completely pure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aroma tischen #-cylsulfonamids, dadurch gekenn- zeichnet, dass man eine Verbindung der Formel EMI0002.0001 auf eine Verbindung der Formel EMI0002.0003 worin X und Y zwei reaktionsfähige, bei der Reaktion mit Ausnahme einer in einem von ihnen enthaltenen NH-Gruppe sich ab spaltende Reste bedeuten, einwirken lässt. PATENT CLAIM: Process for the production of an aromatic # -cylsulfonamide, characterized in that a compound of the formula EMI0002.0001 to a compound of the formula EMI0002.0003 wherein X and Y mean two reactive radicals which split off during the reaction with the exception of an NH group contained in one of them. Die entstandene neue Verbindung, das N - (ss - Naphthoyl) - p - toluolsulfonamid, schmilzt bei 166-168 . UNTERANSPRüCEE 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein ss-Naph- thoes@äurehalogenid auf p-Toluolsulfonamid einwirken lässt. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Kondensationsmittels ausführt. The resulting new compound, the N - (ss - naphthoyl) - p - toluenesulfonamide, melts at 166-168. SUB-CLAIMS 1. Process according to patent claim, characterized in that an ß-naphthoic acid halide is allowed to act on p-toluenesulfonamide. 2. The method according to claim and dependent claim 1, characterized in that the reaction is carried out in the presence of a condensing agent. B. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Katalysators ausführt. 4. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, da-ss man die Reaktion in Gegenwart eines säurebindenden Mittels ausführt. 5. B. The method according to claim and dependent claim 1, characterized in that the reaction is carried out in the presence of a catalyst. 4. The method according to claim and dependent claim 1, characterized in that the reaction is carried out in the presence of an acid-binding agent. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ss-Naphthoe- säure auf p-Toluolsulfonamid in Gegenwart eines Kondensationsmittels einwirken lässt. 6. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein p-Toluol- sulfohalogenid auf ein Salz des ss-Naphthoe- säureamids einwirken lässt. Process according to patent claim, characterized in that β-naphthoic acid is allowed to act on p-toluenesulphonamide in the presence of a condensing agent. 6. The method according to claim, characterized in that a p-toluene sulfohalide is allowed to act on a salt of ß-naphthoic acid amide.
CH255624D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255624A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH255624T 1944-10-25
CH249867T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255624A true CH255624A (en) 1948-06-30

Family

ID=25729400

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255624D CH255624A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255624A (en)

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