CH255627A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

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Publication number
CH255627A
CH255627A CH255627DA CH255627A CH 255627 A CH255627 A CH 255627A CH 255627D A CH255627D A CH 255627DA CH 255627 A CH255627 A CH 255627A
Authority
CH
Switzerland
Prior art keywords
reaction
act
aromatic
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 CH255627A publication Critical patent/CH255627A/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)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

       

  Verfahren     zur    Herstellung eines aromatischen     Acylsulfonamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     aromati-          sehen        Acylsulfonamides-.    Das Verfahren ist  dadurch gekennzeichnet, dass man -eine     Ver-          hindung    der Formel  
EMI0001.0008     
         anf'    eine Verbindung der Formel  
EMI0001.0010     
    worin X     und    Y zwei reaktionsfähige,

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



  Die entstandene neue     Verbindung,    das  <I>(l -</I>     \Taphthoyl)    - 3,4 -     dimethyl    -     benzolsulfon-          amid,    schmilzt bei 180  und     zoll    als Desin  fektionsmittel, z. B. für     Gehrauehsgegen-          ,#tände,    Verwendung finden.  



       Beispiel   <I>1:</I>  18,5 Teile     3,4-Dimethyl-benzolsulfona.mid     werden in 100     Teilen    Nitrobenzol suspen  diert und mit 19 Teilen Aluminiumchlorid  und 19 Teilen     ss-Naphthoesäureehlorid    ver  setzt. Das Gemisch wird     \?    Stunden auf 50   erwärmt     und    hierauf das     Lösungsmittel    mit  Wasserdampf     abdestilliert.    Der Rückstand  wird in     Sodalösung    aufgenommen, mit Tier-         kohle    behandelt und filtriert.

   Aus dem Fil  trat wird das     N-(ss-Naphthoyl)-3,4-dimethyl-          benzols.ulfonamid    mit     Essigsäure    ausgefällt  und durch     Umkristallisieren        aus    Alkohol  gereinigt.  



  Statt unter Zuhilfenahme eines     Konden-          sationc"mittels,    kann die Reaktion auch in  Gegenwart eines säurebindenden     Mittels,     wie z. B. von     Pyridin    oder     Dimethylanilin,     oder in Gegenwart eines     Kaotalysa.tors,    wie  z. B. von Kupferpulver, ausgeführt werden.

      An Stelle eines     Halogenid!s    kann auch  die     freie        ss-Naphthoe-,;äure    in Gegenwatt  eines     Kondensationsmittels    wie     Phosphor-          pentoxyd    oder     Phosphorpentachlorid    verwen  det werden.  



  <I>Beispiel 2:</I>  ?8,6 Teile     ss-Naphthoesäurea-mid    werden  in 200 Teilen absolutem     Xylol        gelöst.    Dann  fügt man 8 Teile     hTatriumamid    hinzu und  erwärmt bis zum Aufhören. der Ammoniak  entwicklung.

   Nach dem Abkühlen gibt man  40,8 Teile     3,4-Dimethyl-benzolsulfochlorid     in 100 Teilen     Xylol    zu und erhitzt mehrere  Stunden unter     Rückf'luss.    Nach beendeter  Reaktion wird das     Xylol    im Vakuum     ab.de-          stilliert.    Der Rückstand wird in     Bicarbonat-          lösung    aufgenommen, mit Tierkohle behan  delt, filtriert und durch     Ansäuern    ausge  fällt.

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



  Process for the preparation of an aromatic acylsulfonamide. The present patent is a process for the preparation of an aromatic see acylsulfonamides. The process is characterized in that there is a compound of the formula
EMI0001.0008
         Anf 'a compound of the formula
EMI0001.0010
    where X and Y are two reactive,

   can act in the reaction with the exception of an NJI group contained in one of them.



  The resulting new compound, the <I> (l - </I> \ Taphthoyl) - 3,4 - dimethyl - benzenesulfonamide, melts at 180 and inches as a disinfectant, e.g. B. for Gehrauehsgegen-, # objects, use.



       Example <I> 1: </I> 18.5 parts of 3,4-dimethyl-benzenesulfona.mid are suspended in 100 parts of nitrobenzene and 19 parts of aluminum chloride and 19 parts of ß-naphthoic acid chloride are added. The mixture will \? Heated to 50 hours and then the solvent was distilled off with steam. The residue is taken up in soda solution, treated with animal charcoal and filtered.

   The N- (ss-naphthoyl) -3,4-dimethylbenzenesulfonamide is precipitated from the filtrate with acetic acid 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, for example, pyridine or dimethylaniline, or in the presence of a Kaotalysa gate, such as, for example, copper powder.

      Instead of a halide, the free β-naphthoic acid can also be used in the counterwatt of a condensing agent such as phosphorus pentoxide or phosphorus pentachloride.



  Example 2: 8.6 parts of ß-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 cessation. the evolution of ammonia.

   After cooling, 40.8 parts of 3,4-dimethylbenzenesulfonyl 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 in bicarbonate solution, treated with animal charcoal, filtered and precipitated by acidification.

   The N- (ss-naphthoyl) -3,4-dimethylbenzenesulfonamide is recrystallized from dilute alcohol and thus obtained completely pure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aroma tischen Acykulfonam.ides, dadureh gekenn- zeichnet, dass man -eine Verbindung der Formel EMI0002.0005 auf eine Verbindung der Formel EMI0002.0007 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 Acykulfonam.ides, dadureh marked that one -a compound of the formula EMI0002.0005 to a compound of the formula EMI0002.0007 wherein X and Y are two reactive radicals which split off in the reaction with the exception of an NH group contained in one of them, can act. Die entstandene neue Verbindung, das N- (,B - Naphthoyl) - 3,4 - ,dimethyl-benzolsulfon- amid, schmilzt bei 180 . UNTERANSPRCCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein ;B-Naph- thoesäurehalogenid auf 3,4-Dimethyl-benzol- sulfonamid einwirken lässt. 2. The resulting new compound, N- (, B - naphthoyl) - 3,4 -, dimethylbenzenesulfonamide, melts at 180. SUB-CLAIM: 1. The method according to claim, characterized in that a; B-naphthoic acid halide is allowed to act on 3,4-dimethyl-benzenesulfonamide. 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. Process according to patent 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. 4th Verfahren nach Patentansprueh und Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in. Gegenwart eines säurebindenden Mittels ausführt. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ss-Na:phthoe- säure auf 3,4-Dimethyl-benzolsulfonamid in Gegenwart eines Kondensationsmittels ein wirken lässt. 6. Process according to patent claim and dependent claim 1, characterized in that the reaction is carried out in the presence of an acid-binding agent. 5. The method according to claim, characterized in that ss-Na: phthoic acid can act on 3,4-dimethylbenzenesulfonamide in the presence of a condensing agent. 6th Verfahren nach -Patentanspruch, da durch gekennzeichnet, dass man ein 3,4-Di- methyl-benzolsulfohalogenid .auf ein Salz des ss-Naphthoesäureamide,s einwirken lässt. A process according to the patent claim, characterized in that a 3,4-dimethyl-benzenesulfohalide is allowed to act on a salt of the β-naphthoic acid amide.
CH255627D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255627A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH249867T 1944-10-25
CH255627T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255627A true CH255627A (en) 1948-06-30

Family

ID=25729403

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255627D CH255627A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255627A (en)

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