CH255612A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

Info

Publication number
CH255612A
CH255612A CH255612DA CH255612A CH 255612 A CH255612 A CH 255612A CH 255612D A CH255612D A CH 255612DA CH 255612 A CH255612 A CH 255612A
Authority
CH
Switzerland
Prior art keywords
reaction
dimethyl
act
dependent
allowed
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 CH255612A publication Critical patent/CH255612A/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)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (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     Acylsulfonamides.            (aegenstarid    vorliegenden Patentes ist ein       @'@@rfahren    zur Herstellung eines     aromati-          @c@encylsulfona.mides.    Das     Verfahren    ist       diadurch    gekennzeichnet,     dass    man     eine        Ver-          l@indung    der     Formel     
EMI0001.0013     
    und eine Verbindung der Formel  
EMI0001.0014     
         worin    X und Y zwei reaktionsfähige,

   bei der  Reaktion mit Ausnahme einer in einem von       ihnen        enthaltenen        NIH-Gruppesieh    abspal  tende Reste bedeuten, aufeinander einwirken  lässt.  



  Die entstandene neue Verbindung, das     N-          (3',4'-        Dimethyl.-        benzoyl)    - 3,4 -     dimethyl-ben-          zol.-ulfonamid,    schmilzt nach Umkristallisa  tion aus Alkohol bei 119 . Sie soll als     Desin-          fektionsmittel,    z. B. für Gebrauchsgegen  stände,     Verwendung    finden.  



  <I>Beispiel 1:</I>  18,5 Teile     3,4-Dimethyl-benzolsulfonamid          arid    15 Teile     3,4-Dimethyl-benzoesäure    wer  den in 200 Teilen Chlorbenzol mit 20 Teilen       Phosphorpentoxyd    4 Stunden unter     Rückfluss          r@ehocht.    Nach dem Erkalten wird das Lö-         sungsmittel    mit     Wasserdampf        abdestilliert     und der Rückstand in     Bicarbonat    gelöst, mit  Tierkohle behandelt, filtriert und mit Essig  säure ausgefällt.

   Das aus     Benzol/Petroläther    ;       kristallisierte        N-(3',4'-Dimethyl-benzoyl)-3,4-          dimethyl-benzolsulfonamidschmilzt    bei 119 .  An     Stelle-    der freien Säure kann auch ein       3,4-Dimethyl-benzoesäure-halogenid    verwen  det und die Reaktion, statt unter Zuhilfe  nahme eines Kondensationsmittels, in Gegen  wart eines säurebindenden     Mittels,    z. B. von       Pyridin    oder     Dimethylanilin,    oder eines Ka  talysators,, z. B. von Kupferpulver, ausge  führt werden.  



       Beispiel   <I>2:</I>  30 Teile     3,4-Dimethyl-benzoesäureamid          mrerden    in 200 Teilen absolutem     Xylol    ge  löst und mit 8 Teilen     Natriumamid    bis zum  Aufhören der     Ammoniakentwicklung    er  wärmt.

   Nach dem Abkühlen fügt man eine  Lösung von 41 Teilen     3,4-Dimethyl-benzol-          sulfochlorid    in 100 Teilen     Xylol    hinzu und  erhitzt mehrere Stunden unter     Rückfluss.     Nach beendeter Reaktion wird das     Lösungs-          mittel    im Vakuum     abdestilliert,    der Rück  stand in     Bicarbonatlösung    aufgenommen, mit  Tierkohle     behandelt,    filtriert und mit Essig  säure ausgefällt.

   Aus     Benzol/Petroläther    um  kristallisiert, ,schmilzt das     N-(3',4'-Dimethyl-          benzoyl)    - 3,4 -     dimethyl-benzolsulf        onamid    bei  119 .



  Process for the preparation of an aromatic acylsulfonamide. (Aegenstarid present patent is a @ '@@ process for the production of an aromati- @ c @ encylsulfona.mide. The process is characterized by the fact that it is a combination of the formula
EMI0001.0013
    and a compound of the formula
EMI0001.0014
         where X and Y are two reactive,

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



  The resulting new compound, N- (3 ', 4'-dimethyl-benzoyl) -3,4-dimethyl-benzene-sulfonamide, melts after recrystallization from alcohol at 119. It should be used as a disinfectant, e.g. B. for commodities, find use.



  <I> Example 1: </I> 18.5 parts of 3,4-dimethylbenzenesulfonamide and 15 parts of 3,4-dimethylbenzoic acid are boiled under reflux for 4 hours in 200 parts of chlorobenzene with 20 parts of phosphorus pentoxide. After cooling, the solvent is distilled off with steam and the residue is dissolved in bicarbonate, treated with animal charcoal, filtered and precipitated with acetic acid.

   That from benzene / petroleum ether; crystallized N- (3 ', 4'-dimethyl-benzoyl) -3,4-dimethyl-benzenesulfonamide melts at 119. Instead of the free acid, a 3,4-dimethylbenzoic acid halide can also be used and the reaction, instead of using a condensing agent, is carried out in the presence of an acid-binding agent, e.g. B. of pyridine or dimethylaniline, or a Ka catalyst ,, z. B. of copper powder, out leads.



       Example <I> 2: </I> 30 parts of 3,4-dimethylbenzoic acid amide are dissolved in 200 parts of absolute xylene and heated with 8 parts of sodium amide until the evolution of ammonia ceases.

   After cooling, a solution of 41 parts of 3,4-dimethylbenzenesulfochloride in 100 parts of xylene is added and the mixture is refluxed for several hours. After the reaction has ended, the solvent is distilled off in vacuo, the residue is taken up in bicarbonate solution, treated with animal charcoal, filtered and precipitated with acetic acid.

   Recrystallized from benzene / petroleum ether, the N- (3 ', 4'-dimethylbenzoyl) -3,4-dimethylbenzenesulfonamide melts at 119.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aromati schen Aeylsulfonamides, dadurch gekvxin- zeichnet, dass man eine Verbindung der Formel EMI0002.0002 und eine Verbindung der Formel EMI0002.0004 worin X und Y zwei reaktionsfähige, bei der Reaktion mit Ausnahme einer in einem von ihnen enthaltenen NN-Gruppe sich abspal tende Reste bedeuten, aufeinander einwirken lässt. PATENT CLAIM: Process for the production of an aromatic Aeylsulfonamides, characterized gekvxin- that one is a compound of the formula EMI0002.0002 and a compound of the formula EMI0002.0004 wherein X and Y mean two reactive radicals which split off during the reaction with the exception of an NN group contained in one of them, can act on one another. Die entstandene neue Verbindung, das N- (3',4' -Dimethyl@-benzoyl)- 3,4 - dimethyl-ben- zolsulfonamid, schmilzt nach Umkristallisa- tion aus Alkohol bei 119 . UNTERANSPRÜCHE 1: Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 3,4-Di- methyl-benzoesäure-halogenid auf 3,4-Di- methyl-benzo:l,aulfonamid einwirken lässt. 2. The resulting new compound, N- (3 ', 4' -dimethyl @ -benzoyl) -3,4-dimethylbenzenesulfonamide, melts at 119 after recrystallization from alcohol. SUBClaims 1: Method according to patent claim, characterized in that a 3,4-dimethylbenzoic acid halide is allowed to act on 3,4-dimethylbenzo: l, aulfonamide. 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, dass man die Reaktion in Gegenwart eines säurebindenden Mittels ausführt. Method according to claim and dependent claim 1, characterized in that one. carrying out the reaction 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 in that the reaction is carried out in the presence of an acid-binding agent. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, da,ss man 3,4-Dimethyl- benzoesäure auf 3,4-Dimethyl-benzolsulfon- amid in Gegenwart eines Kondensationsmit- tels einwirken lässt. 6. 5. The method according to claim, characterized in that 3,4-dimethylbenzoic acid is allowed to act on 3,4-dimethylbenzenesulfonamide in the presence of a condensation agent. 6th Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 3,4-Di- methyl-benzolsulfo-halogenid auf ein .Salz des 3,4-Dimethyl-benzoesäure-amides eimvir- ken lässt. A method according to patent claim, characterized in that a 3,4-dimethyl-benzenesulfo-halide is allowed to be imbaked on a salt of 3,4-dimethyl-benzoic acid amide.
CH255612D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255612A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH249867T 1944-10-25
CH255612T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255612A true CH255612A (en) 1948-06-30

Family

ID=25729388

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255612D CH255612A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255612A (en)

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