CH255622A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

Info

Publication number
CH255622A
CH255622A CH255622DA CH255622A CH 255622 A CH255622 A CH 255622A CH 255622D A CH255622D A CH 255622DA CH 255622 A CH255622 A CH 255622A
Authority
CH
Switzerland
Prior art keywords
reaction
benzenesulfonamide
acylsulfonamide
aromatic
act
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 CH255622A publication Critical patent/CH255622A/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)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

       

  Verfahren zur Herstellung eines aromatischen     Acylsulfonamids.       Gegenstand vorliegenden     Patentes        ist    ein  Verfahren     zurHerstellung        geines    aromatischen       acylsulfonamids.    Das Verfahren ist dadurch       gekennzeichnet,    dass man eine Verbindung  der Formel  
EMI0001.0008     
    auf eine     Verbindung    der     Formel     
EMI0001.0011     
    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-(a-Naphthoyl)-benzol'sulfonamid,        schmilzt     bei     174-.175     und soll als Desinfektionsmit  tel, z. B. für Gebrauchsgegenstände, Verwen  dung finden.         Beispiel   <I>1:</I>    15,7 Teile     Benzol:sulfonamid    werden in  100 Teilen Nitrobenzol suspendiert und mit  19 Teilen     Aluminiumchlorid        und    19 Teilen       cc-Naphthoes-äu@rechlorid    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 - (a -     Na-phthoyl)    -     benzolsulfonamid    mit       Essigsäure    ausgefällt und durch     Umkristal-          linieren    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     a-Naphthoesäure    in     Gegenwart    eines       Kondensationsmittels,    wie     Phosphorpentogyd     oder     Phosphorpentachlorid,    verwendet werden.         Beispiel   <I>2:</I>  28,6 Teile     a-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  35,3     Teile        Benzolsulfochlorid    in 100 Teilen       Xylol    zu und erhitzt mehrere Stunden unter       Rückfluss.    Nach     beendeter    Reaktion wird das       Xylol    im Vakuum     abdestilliert.    Der Rück  stand wird mit     Bikarbonatlösung    aufgenom  men, mit Tierkohle behandelt, filtriert und  durch     Ansäuern        ausgefällt.    Das     N-(a-Naph-          thoyl)

  -benzolsulfonamid    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 acylsulfonamide. The process is characterized in that a compound of the formula
EMI0001.0008
    to a compound of the formula
EMI0001.0011
    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- (a-naphthoyl) -benzene sulfonamide, melts at 174-.175 and is intended as a disinfectant tel, z. B. for everyday objects, find use. Example <I> 1: </I> 15.7 parts of benzene: sulfonamide are suspended in 100 parts of nitrobenzene, and 19 parts of aluminum chloride and 19 parts of cc-naphthoic 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 - (a - Na-phthoyl) - benzenesulfonamide is precipitated from the filtrate with acetic acid and purified from alcohol by recrystallization.



       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, the free α-naphthoic acid can also be used in the presence of a condensing agent, such as phosphorus pentogide or phosphorus pentachloride. Example <I> 2: </I> 28.6 parts of a-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, 35.3 parts of benzenesulfonyl chloride in 100 parts of xylene are added and the mixture is refluxed for several hours. After the reaction has ended, the xylene is distilled off in vacuo. The residue is taken up with bicarbonate solution, treated with animal charcoal, filtered and precipitated by acidification. The N- (a-naphthoyl)

  -benzenesulfonamide is recrystallized from dilute alcohol and thus obtained completely pure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aroma tischen Acylsulfonamids, dadurch gekenn- zeichnet, dass man eine Verbindung der Formel EMI0002.0003 auf eine Verbindung der Formel EMI0002.0004 worin X und Y zwei reaktionsfähige, bei der Reaktion mit Ausnahme einer in einem von ihnen enthaltenen NH-Gruppe sich ab spaltend., Reste bedeuten, einwirken. lässt. Die entstandene neue Verbindung, das N-(a-Naphthoyl)-benzolsulfonamid, schmilzt bei 174-175 . UNTERANSPRüCHE 1. PATENT CLAIM: Process for the production of an aromatic acylsulfonamide, characterized in that a compound of the formula EMI0002.0003 to a compound of the formula EMI0002.0004 wherein X and Y two reactive, in the reaction with the exception of an NH group contained in one of them splitting off., radicals, act. leaves. The resulting new compound, N- (a-naphthoyl) -benzenesulfonamide, melts at 174-175. SUBCLAIMS 1. Verfahren nach Patentanspruch, da durcl gekennzeichnet, dass man ein a-Naph- thoyl-halogenid auf Benzolsulfonamid ein wirken lässt. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Kondensationsmittels ausführt. 3. 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. Process according to patent claim, characterized by the fact that an α-naphthoyl halide is allowed to act on benzenesulfonamide. 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. 3. 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. dass man die Reaktion in Gegenwart eines säurebindenden Mittels ausführt. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man a-Naphthoe- säure auf Benzolsulfonamid in Gegenwart eines Kondensationsmittels einwirken lässt. 6. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein Benzol sulfohalogenid auf ein Salz des a-Napthoe- säureamids einwirken fässt. that the reaction is carried out in the presence of an acid-binding agent. 5. The method according to claim, characterized in that a-naphthoic acid is allowed to act on benzenesulfonamide in the presence of a condensing agent. 6. The method according to claim, characterized in that a benzene sulfohalide acts on a salt of a-naphthoic acid amide.
CH255622D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255622A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH249867T 1944-10-25
CH255622T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255622A true CH255622A (en) 1948-06-30

Family

ID=25729398

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255622D CH255622A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255622A (en)

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