CH255628A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

Info

Publication number
CH255628A
CH255628A CH255628DA CH255628A CH 255628 A CH255628 A CH 255628A CH 255628D A CH255628D A CH 255628DA CH 255628 A CH255628 A CH 255628A
Authority
CH
Switzerland
Prior art keywords
reaction
act
aromatic
dimethyl
naphthoic acid
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 CH255628A publication Critical patent/CH255628A/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)
  • 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)

Description

       

  Verfahren zur Herstellung eines aromatischen     Acylsulfonamides.            CTe",rentand    vorliegenden Patentes ist ein       @'c#rfalircn    zur Herstellung     eines        aromati-          -#clien        Acylsulfonamides.    Das     Verfahren    ist       @!a@lurch        g-\hennzeichnet,    dass man eine     Ver-          bi.ndwil-    der Formel  
EMI0001.0013     
         a.uf        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  spaltende Reste bedeuten, einwirken lässt.  



  Die     entstandene    neue Verbindung, das     N-          (a    -     Naphthoyl)    - 3,4 -     dimethyl    -     benzolsulfon-          amid,    schmilzt bei 140  und soll als     Desin-          fektionsmittel,    z. B. für     Gebrauchsgegen-          st < inde,    Verwendung     finden.     



       Beispiel   <I>1:</I>  18,5 Teile     3,4-Dimethyl-benzolsulfonamid     werden in 100 Teilen Nitrobenzol     Lvuspen-          diert    und mit 19 Teilen     Aluminiumchlorid     und 19 Teilen     a-Naphthoesäurechlorid    ver  setzt.     D &     q Gemisch wird 2     Stunden    auf 50   erwärmt und hierauf     dass    Lösungsmittel mit.

         Wasserdampf        abdestilliert.    Der Rückstand    wird in     Sodalösung    aufgenommen, mit Tier  kohle behandelt und     filtriert.    Aus dem Fil  trat wird das     N-(a-Naphthoyl)-3,4-dimethyl-          benzolsulfonamid    mit Essigsäure ausgefällt  und durch     Umkristallisieren    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        Halogenidss    kann auch  die freie     a-Naphthoe,säure    in Gegenwart  eines     Kondensationsmittelss    wie     Phosphor-          pentoxyd    oder     Phosphorpentachlorid    ver  wendet 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-          e-ntwicklung.    Nach dem Abkühlen gibt man  40,8 Teile     3,

  4-Dimethyl@benzolsulfochlorid     in 100 Teilen     Xylol    zu und erhitzt mehrere  Stunden     unter        Rückfluss.    Nach beendeter  Reaktion wird das     Xylol    im Vakuum     abde-          stilliert.    Der     Rückstand    wird in     Bicarbonat-          lösung    aufgenommen, mit Tierkohle, behan  delt, filtriert und durch Ansäuern ausge  fällt.

   Das     N-(a-Naphthoyl)-3,4-dimethyl-          benzolsulfonamid        wird    aus     verdünntem    Al  kohol     umkristallisiert        und    so völlig rein  erhalten.



  Process for the preparation of an aromatic acylsulfonamide. CTe ", rent and the present patent is a @ 'c # rfalircn for the production of an aromatic - # clien acylsulfonamides. The process is @! A @ lurch g- \ h that one is a combination of the formula
EMI0001.0013
         a. 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 from splitting radicals, can act.



  The resulting new compound, N- (a - naphthoyl) - 3,4 - dimethyl - benzenesulfonamide, melts at 140 and is said to be used as a disinfectant, e.g. B. for utensils, find use.



       Example 1: 18.5 parts of 3,4-dimethylbenzenesulfonamide are suspended in 100 parts of nitrobenzene and 19 parts of aluminum chloride and 19 parts of a-naphthoic acid chloride are added. D & q mixture is heated to 50 for 2 hours and then the solvent with.

         Steam distilled off. The residue is taken up in soda solution, treated with animal charcoal and filtered. The N- (a-naphthoyl) -3,4-dimethylbenzenesulfonamide is precipitated from the Fil with acetic acid and crystallized out. Alcohol cleaned.



  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 pentoxide 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 ammonia development has ceased. After cooling, 40.8 parts of 3 are added

  4-Dimethyl @ benzenesulfochloride in 100 parts of xylene and 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- (a-naphthoyl) -3,4-dimethylbenzenesulfonamide is recrystallized from dilute alcohol and thus obtained completely pure.

Claims (1)

1'ATENTANSPurcll: Verfahren zur Herstellung eines aroma- ti@.schen Acylsulfonamides, dadurch gekenn- zeichnet, dass man eine Verbindung der Formel EMI0002.0010 EMI0002.0011 auf eine Verbindung der Formel worin X und Y zwei reaktionsfähige, 1'ATENTANSPurcll: Process for the production of an aromatic acylsulfonamide, characterized in that a compound of the formula EMI0002.0010 EMI0002.0011 to a compound of the formula wherein X and Y are two reactive, bei der Reaktion mit Ausnahme einer in einem von ihnen enthaltenen NH-Gruppe sich ab spaltende Reste bedeuten, einwirken lässt. Die entstandene neue Verbindung, daG N- (a-Nap@hthoyl) -3,4- dimethyl - benzoIsulfon- amid, schmilzt bei 140 . <B>UNTERANSPRÜCHE:</B> 1. in the reaction, with the exception of an NH group contained in one of them, means from splitting radicals, can act. The resulting new compound, the N- (a-Nap @ thoyl) -3,4-dimethyl-benzo-sulfonamide, melts at 140. <B> SUBClaims: </B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein a-Naph- thoesäurehalbgenid auf 8,4-Dimethyl-benzol- sulfonaanid einwirken lässt. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Kondensationsmittels ausführt. 3. Process according to patent claim, characterized in that an α-naphthoic acid halide is allowed to act on 8,4-dimethylbenzenesulfonaanide. 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. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Katalysators ausführt. 4. Verfahren nach Patentanspruch und Unteransprach 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines säurebindenden Mittels ausführt. 5. Process 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 a-Naphthoe- säure auf 3,4-Dimethyl benzolsulfonamid in Gegenwart eines Kondensationsmittels ein wirken lässt. 6. Verfahren nach Patentanspruch, da- .durch gekennzeichnet, dass man ein 3,4-Di- metUyl-benzolsulfohslogenid auf .ein Salz des a-Naphthoe:säureamides einwirken lässt. Process according to patent claim, characterized in that a-naphthoic acid is allowed to act on 3,4-dimethyl benzenesulfonamide in the presence of a condensing agent. 6. The method according to claim, characterized in that a 3,4-dimethyl-benzenesulfohslogenid is allowed to act on a salt of a-naphthoic acid amide.
CH255628D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255628A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH249867T 1944-10-25
CH255628T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255628A true CH255628A (en) 1948-06-30

Family

ID=25729404

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255628D CH255628A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255628A (en)

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