CH224846A - Process for the preparation of an acylated arylsulfonamide. - Google Patents

Process for the preparation of an acylated arylsulfonamide.

Info

Publication number
CH224846A
CH224846A CH224846DA CH224846A CH 224846 A CH224846 A CH 224846A CH 224846D A CH224846D A CH 224846DA CH 224846 A CH224846 A CH 224846A
Authority
CH
Switzerland
Prior art keywords
arylsulfonamide
acylated
preparation
parts
dichlorobenzenesulfonamide
Prior art date
Application number
Other languages
German (de)
Inventor
A-G J R Geigy
Original Assignee
Geigy Ag J R
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 Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH224846A publication Critical patent/CH224846A/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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Herstellung eines     acylierten        Arylsulfonamides.       Gegenstand des vorliegenden Patentes ist  ein     Verfahren    zur Herstellung eines     acylier-          ten        Arylsulfonamids,    welches dadurch ge  kennzeichnet ist, dass     3,4-Dichlorbenzolsul-          fonamid    oder     ein    Salz desselben mit einem       Butyrylierungsmittel    behandelt wird. Die  neue Verbindung ist     ein    farbloses     Kristall-          pulver    vom F. P. 87 bis 90  .

   Sie dient zur  Bekämpfung von Schädlingen der Insekten  klasse und der Kleinlebewelt.  



  <I>Beispiel:</I>  <B>113</B>     Teile    3,4 -     Dichlorbenzolsulfonamid     werden in 350     Volumteilen    Chlorbenzol  suspendiert, mit 60 Teilen     Butyrylchlorid     und 5 Teilen Kupferpulver versetzt und 12  bis 15 Stunden am     Rückfluss    gekocht.

   Nach  dem Verjagen des Chlorbenzols mit Wasser  dampf wird nach dem Erkalten das in Was  ser unlösliche     3,4-Dichlorbenzolsulfonbutyr-          amid        abfiltriert.    Es zeigt nach dem     Umkri-          stallisieren        aus        wässrigem    Alkohol einen       Schmelzpunkt    von 87 bis<B>90'</B> und besitzt  folgende     Konstitution:     
EMI0001.0028     
    KP.", 225 bis<B>230'.</B>  



  Durch     Zusatz    von Katalysatoren oder  säurebindenden     Mitteln    kann bei der     Butyry-          lierung    des freien Sulfonamids mit     Butyryl-          chlorid    die Ausbeute wesentlich verbessert  werden; es können     Verwendung    finden:

   Kup  ferpulver,     Zinntetrachlorid,        Aluminiumchlo-          rid,    Eisenchlorid,     Berylliumchlorid,    oder     calc.     Soda,     Calciumcarbonat,        Pyridin,        Dimethyl-          anilin        etc.    Statt des freien Sulfonamids  kann man mit Vorteil zum Beispiel das Na  triumsalz verwenden.



  Process for the preparation of an acylated arylsulfonamide. The subject of the present patent is a process for the preparation of an acylated arylsulfonamide, which is characterized in that 3,4-dichlorobenzenesulfonamide or a salt thereof is treated with a butyrylating agent. The new compound is a colorless crystal powder from F. P. 87 to 90.

   It is used to control pests of the insect class and small organisms.



  <I> Example: </I> <B> 113 </B> parts of 3,4-dichlorobenzenesulfonamide are suspended in 350 parts by volume of chlorobenzene, 60 parts of butyryl chloride and 5 parts of copper powder are added and the mixture is refluxed for 12 to 15 hours.

   After the chlorobenzene has been chased off with steam, the 3,4-dichlorobenzenesulfonobutyramide, which is insoluble in water, is filtered off after cooling. After recrystallization from aqueous alcohol, it has a melting point of 87 to 90 'and has the following constitution:
EMI0001.0028
    KP. ", 225 to <B> 230 '. </B>



  By adding catalysts or acid-binding agents, the yield can be significantly improved in the butyrylation of the free sulfonamide with butyryl chloride; it can be used:

   Copper powder, tin tetrachloride, aluminum chloride, iron chloride, beryllium chloride, or calc. Soda, calcium carbonate, pyridine, dimethyl aniline, etc. Instead of the free sulfonamide, it is advantageous to use the sodium salt, for example.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines acylier- ten Arylsulfonamids, dadurch gekennzeich net, dass man 3,4-Dichlorbenzolsulfonamid oder ein Salz desselben mit einem Butyrylie- rungsmittel behandelt. Die neue Verbindung ist ein farbloses Kristallpulver vom F. P. 87 bis<B>90'.</B> Sie dient zur Bekämpfung von Schädlingen der Insektenklasse und der Kleinlebewelt. PATENT CLAIM: Process for the preparation of an acylated arylsulfonamide, characterized in that 3,4-dichlorobenzenesulfonamide or a salt thereof is treated with a butyrylating agent. The new compound is a colorless crystal powder from F. P. 87 to <B> 90 '. </B> It is used to control pests of the insect class and the small world.
CH224846D 1940-02-02 1940-02-02 Process for the preparation of an acylated arylsulfonamide. CH224846A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH220746T 1940-02-02
CH224846T 1940-02-02

Publications (1)

Publication Number Publication Date
CH224846A true CH224846A (en) 1942-12-15

Family

ID=25726482

Family Applications (1)

Application Number Title Priority Date Filing Date
CH224846D CH224846A (en) 1940-02-02 1940-02-02 Process for the preparation of an acylated arylsulfonamide.

Country Status (1)

Country Link
CH (1) CH224846A (en)

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