CH255623A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

Info

Publication number
CH255623A
CH255623A CH255623DA CH255623A CH 255623 A CH255623 A CH 255623A CH 255623D A CH255623D A CH 255623DA CH 255623 A CH255623 A CH 255623A
Authority
CH
Switzerland
Prior art keywords
reaction
toluenesulfonamide
aromatic
compound
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 CH255623A publication Critical patent/CH255623A/en

Links

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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Description

       

  Verfahren zur Herstellung eines aromatischen     Acylsulfonamids.       Gegenstand vorliegenden Patentes     ist    ein  Verfahren zur Herstellung eines     aromatischen          Aevlsulfonamids.    Das Verfahren ist dadurch       g;el@ennzciehnet,    dass man eine     Verbindung          dei-        Formel          CHü-@@-SO@-X          911f    eine     Verbindung    der Formel       Y-OC-CH.:

          - < D     worin X und Y zwei reaktionsfähige, bei der       sseaktion    mit     Ausnahme    einer in einem  von ihnen enthaltenen HH-Gruppe sich ab  spaltende Reste bedeuten, einwirken     lä.sst.     



  Die entstandene neue Verbindung, das  X -     (Phenyl    -     acetj-1)    - p -     toluolsulfonamid,          schmilzt    bei     133-135     und soll als     Desinfek-          tionsmittel,    z. B. für Gebrauchsgegenstände,       Vc@r@vendung    finden.  



       Beispiel   <I>1:</I>  17,1 Teile     p-Toluolsulfonamid    werden in  100 Teilen Nitrobenzol .suspendiert und mit  19 Teilen Aluminiumchlorid und 15,4 Teilen       Plienyl'(-ssigsäurechlorid    versetzt. Das     Ge-          iniscli    wird ? Stunden auf 50  erwärmt und  hierauf das     Lösunbsmittel    mit     Wasserdampf          abdestilliert.    Der Rückstand wird in Soda  lösung aufgenommen, mit Tierkohle behan  delt     und    filtriert.

   Aus dem Filtrat wird das       ;\-(Plienyl-acetcl)-p-toluolsulfonamid    mit    Essigsäure ausgefällt und durch     Umkristal-          lisieren    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     Halogenids    kann auch die  freie     Phenylessigsäure    in Gegenwart eines       Kondensationsmittels,    wie     Phos:phorpentoxyd     oder     Phosphorpentachlorid,    verwendet werden.  <I>Beispiel 2:</I>       ?2,9    Teile     Phenylessigsäureamid    werden  in 200 Teilen absolutem     Xyl'ol    gelöst. Dann  fügt man 8 Teile     Natriumamid    hinzu und  erwärmt bis zum Aufhören der Ammoniak  entwieklung.

   Nach dem Abkühlen gibt man  38 Teile     p-Toluolsulfochlorid    in 100 Teilen       Xylol    zu und erhitzt mehrere Stunden unter       Rückfluss.    Nach beendeter Reaktion     wird    das       Xyl'ol    im Vakuum     abdestilliert.    Der Rück  stand wird in     ssikarbonatlösung    aufgenom  men, mit Tierkohle behandelt,     filtriert    und  durch     Ansäuern    ausgefällt. Das     N-(Phenyl-          acetyl)-p-toluolsulfonamid    wird aus verdünn  tem Alkohol     umkristallisiert    und so völlig  rein erhalten.



  Process for the preparation of an aromatic acylsulfonamide. The present patent relates to a process for the preparation of an aromatic sulfonamide. The method is g; el @ ennzciehnet that a compound of the formula CHü - @@ - SO @ -X 911f a compound of the formula Y-OC-CH .:

          - <D where X and Y mean two reactive radicals which split off in the reaction with the exception of one HH group contained in one of them.



  The resulting new compound, the X - (phenyl - acetj-1) - p - toluenesulfonamide, melts at 133-135 and is said to be used as a disinfectant, e.g. B. for everyday objects, find Vc @ r @ use.



       Example <I> 1: </I> 17.1 parts of p-toluenesulfonamide are suspended in 100 parts of nitrobenzene and 19 parts of aluminum chloride and 15.4 parts of plienyl acid chloride are added The residue is taken up in soda solution, treated with animal charcoal and filtered.

   The; \ - (Plienyl-acetyl) -p-toluenesulfonamide is precipitated from the filtrate with acetic acid and purified from alcohol by recrystallization.



  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 phenylacetic acid can also be used in the presence of a condensing agent such as phosphorus pentoxide or phosphorus pentachloride. <I> Example 2: </I> 2.9 parts of phenylacetic 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 has stopped developing.

   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 ssikarbonatlösung men, treated with animal charcoal, filtered and precipitated by acidification. The N- (phenylacetyl) -p-toluenesulfonamide is recrystallized from dilute alcohol and thus obtained completely pure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aroma tischen Acylsulfonamids, dadurch gekenn- zeichnet, dass man eine Verbindung der Formel EMI0002.0004 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 EMI0002.0004 to a compound of 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 - (Phenyl - acetyl) - p - toluolsulfonamid, schmilzt bei 133-135 . UNTERANSPRÜCEE: 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein Phenyl- essigsäurehalogenid auf p-Toluolsulfonamid einwirken lässt. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eins Kondensationsmittels ausführt. 3. The resulting new compound, N - (phenyl - acetyl) - p - toluenesulfonamide, melts at 133-135. SUB-CLAIMS: 1. Process according to patent claim, characterized in that a phenylacetic acid halide is allowed to act on p-toluenesulfonamide. 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 Unterans pruch 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 patent claim and sub-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 Phenylessib .säure auf p-Toluolsulfonamid in Gegenwart eines Kondensationsmittels einwirken lä.sst. 6. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein p-Toluol- sulfoha-Iagenid auf ein Salz des Phenylessig- säureamids einwirken lässt. Process according to patent claim, characterized in that phenylessib. 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 sulfoha Iagenid is allowed to act on a salt of phenyl acetic acid amide.
CH255623D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255623A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH255623T 1944-10-25
CH249867T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255623A true CH255623A (en) 1948-06-30

Family

ID=25729399

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255623D CH255623A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255623A (en)

Similar Documents

Publication Publication Date Title
DE1112074B (en) Process for the preparation of thiophosphoric acid esters
CH255623A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255625A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255624A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255622A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255627A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255630A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255628A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255629A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255626A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255615A (en) Process for the preparation of an aromatic acylsulfonamide.
CH249867A (en) Process for the preparation of an aromatic acylsulfonamide.
DE955510C (en) Process for the preparation of a heterocyclic quinone
CH255614A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255612A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255616A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255621A (en) Process for the preparation of an aromatic acylsulfonamide.
CH255610A (en) Process for the preparation of an aromatic acylsulfonamide.
CH264506A (en) Process for the preparation of an acylated p-amino-benzenesulfonamide.
CH264504A (en) Process for the preparation of an acylated p-amino-benzenesulfonamide.
CH137740A (en) Process for the preparation of 1,4-dioxy-benzo-thiophanthrenequinone.
CH255619A (en) Process for the preparation of an aromatic acylsulfonamide.
CH310710A (en) Process for the preparation of an organic salt of hydrofluoric acid.
CH253170A (en) Process for the preparation of a p-amino-benzene-sulfonacylamide.
CH255617A (en) Process for the preparation of an aromatic acylsulfonamide.