CH255625A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

Info

Publication number
CH255625A
CH255625A CH255625DA CH255625A CH 255625 A CH255625 A CH 255625A CH 255625D A CH255625D A CH 255625DA CH 255625 A CH255625 A CH 255625A
Authority
CH
Switzerland
Prior art keywords
reaction
aromatic
acylsulfonamide
toluenesulfonamide
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 CH255625A publication Critical patent/CH255625A/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.            Gegenstand    vorliegenden Patentes ist ein       \"erfahren    zur Herstellung eines     aromati-          chen        Aeylsulfonamides,.    Das Verfahren ist       dadurch    gekennzeichnet,     da.ss        man    eine     Ver-          liinduug    der Formel  
EMI0001.0012     
         auf    eine Verbindung der Formel  
EMI0001.0014     
    worin X und Y zwei reaktionsfähige,

   bei  der Reaktion     mit    Ausnahme einer in einem  <B>VOR</B> ihnen enthaltenen     NH-Gruppe    sich ab  paltende Reste bedeuten, einwirken lässt.  



  Die     entstandene    neue Verbindung, das     N-          (a-Naplithoyl)-p-toluolsulfonamid,    schmilzt       Iyui    150  und soll als     Desinfektionsmittel,          z.        B.    für     Gebrauchsgegenstände.        Verwen-          dung;    finden.  



  <I>Beispiel 1:</I>  <B>17,1</B> Teile     p-Toluolsulfona.mid    werden in  100 Teilen     Nitrobenzol    suspendiert und mit  19 Teilen     Aluminiumchlorid    und 19 Teilen       a-N        al)hthoesäurechlorid    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       17    - (a -     Naphthoyl)    -     p    -     toluol:sulfonamid    mit         Essigsäure    ausgefällt und durch     I:mkristal-          lisieren    aus Alkohol     gereinigt.     



  Statt unter Zuhilfenahme eines     Konden-          ationsmittels,    kann die Reaktion auch in  s<B>s</B>  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    Phosphor  pentogyd oder     Phosphorpentaehlorid    ver  wendet werden.  



       Beispiel   <I>2:</I>  28,6 Teile     a-Naphthoesäureamid    werden  in 200 Teilen absolutem     Xylol    gelöst. Dann  fügt man 8 Teile     @Ta:triumamid    hinzu und  erwärmt bis zum Aufhören der Ammoniak  entwicklung.

   Nach     dem    Abkühlen     gibt    man  38     Teile        p-Toluolsulfochlorid    in<B>100</B> Teilen       Xylol    zu und erhitzt mehrere Stunden unter       Rückfluss.    Nach beendeter     Reaktion    wird  das     Xylol    im Vakuum     abdestilliert.    Der  Rückstand wird in     Bicarbonatlösung    auf  genommen, mit Tierkohle behandelt, filtriert  und durch     Ansäaiern    ausgefällt.

   Das     N-          (a-Na.phthoyl)-p-toluolsulfona,mid        wird    aus  verdünntem Alkohol     umkristallisiert    und so  völlig rein erhalten.



  process for the production of an aromatic acylsulfonamide. The subject of the present patent is an experience in the preparation of an aromatic alkylsulfonamide. The process is characterized in that a mixture of the formula is obtained
EMI0001.0012
         to a compound of the formula
EMI0001.0014
    where X and Y are two reactive,

   can act in the reaction with the exception of an NH group contained in a <B> VOR </B> them meaning splitting radicals.



  The resulting new compound, the N- (a-naplithoyl) -p-toluenesulfonamide, melts Iyui 150 and is said to be used as a disinfectant, e.g. B. for everyday objects. Use; Find.



  <I> Example 1: </I> <B> 17.1 </B> parts of p-Toluolsulfona.mid are suspended in 100 parts of nitrobenzene, and 19 parts of aluminum chloride and 19 parts of α-N al) thoic 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 17 - (a - naphthoyl) - p - toluene: sulfonamide is precipitated from the filtrate with acetic acid and purified from alcohol by crystallization.



  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 pentogyd or phosphorus pentoxide.



       Example <I> 2: </I> 28.6 parts of a-naphthoic acid amide are dissolved in 200 parts of absolute xylene. Then 8 parts of @Ta: triumamide are added and the mixture is heated until the ammonia development stops.

   After cooling, 38 parts of p-toluenesulfonyl 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- (a-Na.phthoyl) -p-toluenesulfona, mid is recrystallized from dilute alcohol and thus obtained completely pure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aroma tischen Acylsulfonamides, dadurch gek-enn- zeichnet, dass man eine Verbindung der Formel EMI0002.0002 auf eine Verbindung :der Formel EMI0002.0005 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 acylsulfonamide, characterized in that a compound of the formula EMI0002.0002 on a compound: the formula EMI0002.0005 wherein X and Y mean two reactive radicals which split off during the reaction with the exception of an NH group contained in one of them. Die entstandene neue Verbindung, das N- (a-Naphthoyll) -p-toluolsulfonamid, schmilzt bei 150 . UNTERANSPRÜCHE: 1. Verfahren nach Patentauspruch, da durch gekennzeichnet, dass man ein a-Naph- thoesäurehallogenid auf p-Toluolsulfonamid einwirken lässt. 2. The resulting new compound, N- (a-naphthoyl) -p-toluenesulfonamide, melts at 150. SUBClaims: 1. Method according to patent claim, characterized in that an α-naphthoic acid halide is allowed to act on p-toluenesulfonamide. 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. 5. Process 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 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 p-Toluolsulfonamid in Gegenwart eines Kondensationsmittels einwirken lässt. 6. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein p-Toluol- sulfGhalogenid 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 p-toluenesulfonamide in the presence of a condensing agent. 6. The method according to claim, characterized in that a p-toluene sulfGhalide is allowed to act on a salt of the a-naphthoic acid amide.
CH255625D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255625A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH255625T 1944-10-25
CH249867T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255625A true CH255625A (en) 1948-06-30

Family

ID=25729401

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255625D CH255625A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255625A (en)

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