CH255626A - Process for the preparation of an aromatic acylsulfonamide. - Google Patents

Process for the preparation of an aromatic acylsulfonamide.

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Publication number
CH255626A
CH255626A CH255626DA CH255626A CH 255626 A CH255626 A CH 255626A CH 255626D A CH255626D A CH 255626DA CH 255626 A CH255626 A CH 255626A
Authority
CH
Switzerland
Prior art keywords
sep
act
reaction
process according
acid
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 CH255626A publication Critical patent/CH255626A/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)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (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)

Description

       

  Verfahren zur Herstellung eines aromatischen     Acylsulfonamides.     
EMI0001.0002     
  
    Gegenstand <SEP> vorliegenden <SEP> Patentes <SEP> ist <SEP> ein
<tb>  Verfahren. <SEP> zur <SEP> Herstellung <SEP> eines <SEP> aromati  sulien <SEP> Acylsulfonamides.. <SEP> Das <SEP> Verfahren <SEP> ist
<tb>  dadurch <SEP> gekennzeichnet, <SEP> dass <SEP> man <SEP> eine <SEP> Ver  1)iiidnn_ <SEP> der <SEP> Formel     
EMI0001.0003     
  
EMI0001.0004     
  
    ;

  11i1' <SEP> tähie <SEP> Verbindung <SEP> der <SEP> Formel     
EMI0001.0005     
         cvorin    X und Y zwei reaktionsfähige, bei       iler        Reaktion    mit Ausnahme einer in einem  von ihnen enthaltenen     NH-Gruppe    sich     ab-          s13allende    Reste     bedeuten,    einwirken lässt.  



  Die     entstandene    neue     Verbindung,    das     N-          (3-:3,lethoxy-naphthoyl'-        (2)]        -,p-toluolsulfon-          aniid,        .schmilzt    bei 158-160  und     soll    als       Desinfektionsmittel,    z. B. für     Gebrauchs-          fVeg        enstände,        Verwendung    finden.  



       Beispiel   <I>1:</I>  17,1 Teile     p-Toluolsulfona.mid    werden in  100     Teilen    Nitrobenzol     siuspendiert    und mit  <B>19</B> Teilen Aluminiumchlorid und 22     Teilen          :1-1-refaioxy        -naphthoesäure-(?)        -chlorid        ver-          sf.tzt.        Da.s    Gemisch wird 2 Stunden auf 50        erwärmt    und hierauf das Lösungsmittel mit       Wasserdampf        a;

  bdestilliert.    Der Rückstand        -irl    in     Soda.lösung    aufgenommen, mit     Tier-          lzohle        behandelt    und filtriert. Aus dem Fil-    trat wird das     N-[3-Methoxy-naphthoyl-(2)]-          p-toluo-Isulfonamid    mit     Essig        'äure    ausgefällt  und durch     LTmkristallisieren        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     Hülogenids    kann auch  die freie     3-Methoxy-naphthoesäure-(2)    in .  Gegenwart eines     Kondensationsmittels    wie       PhosphoTpe:ntoxyd    oder     P'hosphorpentachlo-          rid    verwendet werden.  



  <I>Beispiel. 2:</I>  33,7 Teile     3-Methoxy-naphthoesäure-(2)-          amid        werden    in 200 Teilen absolutem     Xyl'ol     gelöst. Dann fügt man 8 Teile     Natriumaimid     hinzu und     erwärmt        biss    zum Aufhören der       Ammoniakentwicklung.    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     Xylol    im Vakuum 

      abde-          stilliert.    Der Rückstand wird in     Bicarbonat-          lösung    aufgenommen, mit Tierkohle behan  delt,     filtriert    und durch     Ansäuern.    ausge  fällt. Das     N-[3-Methoxy'-naphthoyl-(2)]-p-          toluolsulfona;mid    wird aus     verdünntem    Al  kohol umkristallisiert und so     völlig    rein  erhalten.



  Process for the preparation of an aromatic acylsulfonamide.
EMI0001.0002
  
    The subject of <SEP> present <SEP> patent <SEP> is <SEP> a
<tb> procedure. <SEP> for <SEP> production <SEP> of an <SEP> aromatic <SEP> acylsulfonamides .. <SEP> The <SEP> process <SEP> is
<tb> characterized by <SEP>, <SEP> that <SEP> man <SEP> a <SEP> Ver 1) iiidnn_ <SEP> of the <SEP> formula
EMI0001.0003
  
EMI0001.0004
  
    ;

  11i1 '<SEP> tähie <SEP> connection <SEP> of the <SEP> formula
EMI0001.0005
         cvorin X and Y are two reactive residues which, in the event of an iler reaction, with the exception of an NH group contained in one of them, represent falling radicals.



  The resulting new compound, the N- (3-: 3, lethoxy-naphthoyl'- (2)] -, p-toluenesulphonic aniide, melts at 158-160 and is intended as a disinfectant, e.g. for consumer goods arises, find use.



       Example <I> 1: </I> 17.1 parts of p-Toluolsulfona.mid are suspended in 100 parts of nitrobenzene and mixed with <B> 19 </B> parts of aluminum chloride and 22 parts: 1-1-refaioxy -naphthoic acid- ( ?) chloride depleted. Da.s mixture is heated to 50 for 2 hours and then the solvent with steam a;

  distilled. The residue is taken up in soda solution, treated with animal charcoal and filtered. The N- [3-methoxy-naphthoyl- (2)] - p-toluo-isulphonamide is precipitated from the filtrate with acetic acid and purified by crystallization 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 B. of pyridine or dimethylaniline, or in the presence of a catalyst, such as. B. of copper powder.



  Instead of a Hülogenid, the free 3-methoxynaphthoic acid (2) in. Presence of a condensation agent such as PhosphoTpe: ntoxyd or P'hosphorpentachlo- rid can be used.



  <I> example. 2: 33.7 parts of 3-methoxynaphthoic acid (2) 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 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 in vacuo

      distilled. The residue is taken up in bicarbonate solution, treated with animal charcoal, filtered and acidified. failed. The N- [3-methoxy'-naphthoyl- (2)] - p-toluenesulfona; mid is recrystallized from dilute alcohol and thus obtained completely pure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines aroma, tischen Acylsulfonamides, dadurch gekenn- zeichnet, da-ss man eine Verbindung der Formel EMI0002.0009 auf eine Verbindung .der Formel EMI0002.0012 worin X und Y zwei reaktionsfähige, PATENT CLAIM: Process for the production of an aromatic acylsulfonamide, characterized in that a compound of the formula EMI0002.0009 to a compound of the formula EMI0002.0012 where X and Y are two reactive, bei der Reaktion mit Ausnahme einer in einem von. ihnen enthaltenen NH=Gruppe sieh ab spaltende Reste bedeuten, einwirken lässt. Die entstandene neue Verbindung, das. N- 13 -Methoxy-naphthoyl - (2)1 -p,-toluol;sulf on- amid, schmilzt bei 158-160 . UNTERANSPRüCHE 1. in response except one in one of. they contain NH = group see off splitting residues mean, can act. The resulting new compound, the. N-13 -methoxy-naphthoyl- (2) 1 -p, -toluene; sulfonamide, melts at 158-160. SUBCLAIMS 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein 3-Meth- oxy - naphthoesäure - (2) - halogenid auf p Toluolsulfonamid einwirken lässt. <B>.</B> Verfahren nach Patentanspruch und 21 Unteranspruch 1, dadurch gekennzeichnet, dass man die Reaktion in Gegenwart eines Kondensationsmittels ausführt. 3. Process according to patent claim, characterized in that a 3-methoxynaphthoic acid (2) halide is allowed to act on p toluenesulfonamide. <B>. </B> Process 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 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 catalyst. executes. 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 3-Methoxy- naphthoesäure-(2) auf p-Toluolsulfonamid in Gegenwart eines Kondensationsmittels einwirken lässt. 6. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man ein p-Toluol- sulfohalogenid auf ein Salz des 3-Methoxy- naPhthoessäure-(2)-amides einwirken lässt. Process according to patent claim, characterized in that 3-methoxynaphthoic acid (2) 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 sulfohalide is allowed to act on a salt of 3-methoxy- naPhthoessäure- (2) -amides.
CH255626D 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide. CH255626A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH249867T 1944-10-25
CH255626T 1944-10-25

Publications (1)

Publication Number Publication Date
CH255626A true CH255626A (en) 1948-06-30

Family

ID=25729402

Family Applications (1)

Application Number Title Priority Date Filing Date
CH255626D CH255626A (en) 1944-10-25 1944-10-25 Process for the preparation of an aromatic acylsulfonamide.

Country Status (1)

Country Link
CH (1) CH255626A (en)

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