CH255613A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

Info

Publication number
CH255613A
CH255613A CH255613DA CH255613A CH 255613 A CH255613 A CH 255613A CH 255613D A CH255613D A CH 255613DA CH 255613 A CH255613 A CH 255613A
Authority
CH
Switzerland
Prior art keywords
reaction
act
methyl
benzoic acid
aromatic
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 CH255613A publication Critical patent/CH255613A/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     Acylsulfonamides.       Gegenstand vorliegenden Patentes ist ein       Verfahren    zur Herstellung     eines        aromati-          sehen        Aeylsulfona.mides.    Das Verfahren ist       dadurch    gekennzeichnet,     dass    man eine     Ver-          Undung    der     Formel     
EMI0001.0012     
    auf eine Verbindung der Formel  
EMI0001.0013     
    worin X und Y     reaktionsfähige,

      bei der Re  aktion mit Ausnahme einer in einem von  ihnen enthaltenen     NH-Gruppe    sich abspal  tende Reste bedeuten, einwirken lässt.  



  Die entstandene neue     Verbindung,    das N  (4'-llethylmereapto:-benzoyl)     -4-methyl-ben-          zolsulfonamid,    schmilzt nach Umkristallisa  tion bei 180 . Sie soll als     Desinfektionsmittel.     z. B. für     Gebrauchsgegenstände,    Verwendung  finden.  



       Beispiel        .T     <B>17,1</B> Teile     4-1@Z-ethyl-benzolsulfonamid    und  <B>16,8</B> Teile     4-Methylmercapto-benzoe:aäure     werden in 200 Teilen Chlorbenzol mit 20  Teilen     Phosphorpentoxyd    4 Stunden     unter          Rückfluss    gekocht. Nach dem Erkalten wird  das Lösungsmittel mit Wasserdampf ab  destilliert und der Rückstand in     Bicarbonat     gelöst., mit Tierkohle behandelt,     filtriert    und  mit Essigsäure ausgefällt.

   Das aus Benzol/       Petroläther    umkristallisierte     N-(4'-Methyl-          mercapto    -     benzoyl)    - 4 -     methyl    -     benzolsulfon-          a.mid    schmilzt bei 180 .    An Stelle der freien Säure kann auch ein       4-lllethylmeroapto-benzoesäure-halogenid    ver  wendet     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>    33,5 Teile     4-Methylmercapto-benzoesäure-          amid    werden in 200 Teilen     absolutem        Xylol     gelöst und mit 8 Teilen     Natriumamid    bis  zum Aufhören der     Ammoniakentwicklung     erwärmt.

   Nach dem Abkühlen fügt man     eine     Lösung von 3<B>8</B> Teilen     4-1Tethyl-benzolsulfo-          ehlorid    in 100 Teilen     Xylol        hinzu    und er  hitzt mehrere Stunden unter     Rückfluss.    Nach  beendeter Reaktion wird das     Lösungsmittel     im Vakuum     abdestilliert,    der Rückstand in       Bicarbonatlösung    aufgenommen, mit Tier  kohle behandelt, filtriert und mit     Esisigsäure     ausgefällt.

   Aus     Benzol/Petroläther        umkri-          stallisiert,    schmilzt das     N-(4-Methylmer-          capto-benzoyl)-4-methyl-benzolsulfonamid    bei  180 .



  Process for the preparation of an aromatic acylsulfonamide. The present patent is a process for the preparation of an aromatic see Aeylsulfona.mides. The method is characterized in that one undulation of the formula
EMI0001.0012
    to a compound of the formula
EMI0001.0013
    where X and Y are 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, N (4'-llethylmereapto: -benzoyl) -4-methylbenzenesulfonamide, melts at 180 after recrystallization. They are said to be used as a disinfectant. z. B. for everyday objects, use.



       Example .T 17.1 parts 4-1 @ Z-ethyl-benzenesulfonamide and 16.8 parts 4-methylmercaptobenzoic acid in 200 parts chlorobenzene with 20 parts Phosphorus pentoxide refluxed for 4 hours. 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.

   The N- (4'-methyl-mercapto-benzoyl) -4-methyl-benzenesulfon-a.mid recrystallized from benzene / petroleum ether melts at 180. Instead of the free acid, a 4-lllethylmeroapto-benzoic acid halide can be used and the reaction, instead of using a condensing agent, in the presence of an acid-binding agent, e.g.

   B. of pyridine or dimethylaniline, or a catalyst, z. B. of copper powder, out leads. Example <I> 2: </I> 33.5 parts of 4-methylmercapto-benzoic 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 3 8 parts of 4-1-ethylbenzenesulfonyl chloride in 100 parts of xylene is added and it 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- (4-methylmercapto-benzoyl) -4-methyl-benzenesulfonamide melts at 180.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aromati schen Acylsulfonamides, dadurch gekenn zeichnet, dass man eine Verbindung der Formel EMI0001.0070 auf eine Verbindung der Formel EMI0002.0001 worin X und Y reaktionsfähige, bei der Re aktion mit Ausnahme einer in einem von ihnen enthaltenen NN-Gruppe sich abspal tende Reste bedeuten, einwirken lässt. PATENT CLAIM: Process for the preparation of an aromatic acylsulfonamide, characterized in that a compound of the formula EMI0001.0070 to a compound of the formula EMI0002.0001 wherein X and Y reactive radicals which split off during the reaction with the exception of an NN group contained in one of them mean, can act. Die entstandene neue Verbindung, das N- (4' - Methylmercapto-benzoyl) -4 - methyl - ben- zolsulfonamid, schmilzt nach Umkristallisa tion bei 180 . UNTERANSPRÜCHE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 4-Methyl- mercapto-benzoesäure-halogenid auf 4-Me- thylbenzoIsulfonamid einwirken lässt. The resulting new compound, N- (4'-methylmercapto-benzoyl) -4-methyl-benzenesulfonamide, melts at 180 after recrystallization. SUBClaims: 1. Method according to patent claim, characterized in that a 4-methyl mercapto-benzoic acid halide is allowed to act on 4-methyl benzo-sulfonamide. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet. dass man die Reaktion in Gegenwart eines Kondensationsmittels ausführt. 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. 2. The method according to claim and dependent claim 1, characterized. that the reaction is carried out in the presence of a condensing agent. 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. dass man die Reaktion in Gegenwart eines säurebindenden Mittels ausführt. 5. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man 4-Methylmer- capto-benzoesäure auf 4-Methyl-benzolsulfon- amid in Gegenwart eines Kondensationsmit tels einwirken lässt. 6. that the reaction is carried out in the presence of an acid-binding agent. 5. The method according to claim, characterized in that 4-methylmer-capto-benzoic acid is allowed to act on 4-methyl-benzenesulfonamide in the presence of a condensation agent. 6th Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 4-Methyl- benzolsulfo-halogenid auf ein Salz des 4-Me- thylmercapto-benzoesäure-amides einwirken lässt. Process according to patent claim, characterized in that a 4-methylbenzenesulfo-halide is allowed to act on a salt of the 4-methylmercapto-benzoic acid amide.
CH255613D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255613A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH255613T 1944-10-25
CH249867T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255613A true CH255613A (en) 1948-06-30

Family

ID=25729389

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255613D CH255613A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255613A (en)

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