CH246983A - Process for the preparation of a 4-chloro-benzenesulfonamide. - Google Patents

Process for the preparation of a 4-chloro-benzenesulfonamide.

Info

Publication number
CH246983A
CH246983A CH246983DA CH246983A CH 246983 A CH246983 A CH 246983A CH 246983D A CH246983D A CH 246983DA CH 246983 A CH246983 A CH 246983A
Authority
CH
Switzerland
Prior art keywords
chloro
preparation
benzenesulfonamide
amide
dimethyl
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 CH246983A publication Critical patent/CH246983A/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        4-Chlor-benzolsulfonamides.       Gegenstand vorliegenden Patentes ist ein  Verfahren zur Herstellung eines     4-Chlor-          benzolsulfonamides.    Das Verfahren ist da  durch gekennzeichnet, dass man     4-Amino-          benzolsulfon-N-dimethyl-amid        diazotiert    und  die     Diazogruppe    mit     Kupfer(I)-chlorid    und  Salzsäure durch Chlor ersetzt.

   Die entstan  dene neue     Verbindung,    das     4-Chlor-benzol-          sulfon-N-dimethyl-amid,        bildet    farblose     Kri-          stalle    vom     Schmelzpunkt    80  und siedet unter  einem Druck von 0,05 mm bei     140 .    Sie soll  als     Milbenbekämpfungsmittel    (sowohl für       freilebende    als auch für parasitisch lebende  Milben)     Verwendung    finden.  



       Beispiel:     20 Teile     4-Amino-benzolsulfon-N-di-          methyl-amid    werden in salzsaurer Lösung  in üblicher Weise     diazotiert    und die     Diazo-          lösung        portionenweise    bei Raumtemperatur  zu 10 Teilen     Kupfer(I)-chlorid    in 30     Volum-          teile    konzentrierte Salzsäure gegeben.

   Nach    beendeter Zugabe wird noch     i/4        Stunde    auf  50-60      erwärmt,    dann erkalten gelassen  und das     4-Chlor-benzolsulfon-N-dimethyl-          amid'    mit Äther     ausgezogen.    Nach Ab  dampfen des Äthers verbleibt ein     braunes    01,  das im Hochvakuum     unter    einem Druck von  0,05 mm bei 140  destilliert und in der       gälte    erstarrt. Es bildet farblose Kristalle  vom     Schmelzpunkt    80 .



      Process for the preparation of a 4-chloro-benzenesulfonamide. The present patent is a process for the preparation of a 4-chlorobenzenesulfonamide. The process is characterized in that 4-aminobenzenesulfone-N-dimethyl-amide is diazotized and the diazo group is replaced with copper (I) chloride and hydrochloric acid by chlorine.

   The resulting new compound, 4-chloro-benzenesulfone-N-dimethyl-amide, forms colorless crystals with a melting point of 80 and boils at 140 under a pressure of 0.05 mm. It should be used as a mite control agent (for both free-living and parasitic mites).



       Example: 20 parts of 4-amino-benzenesulfon-N-dimethyl-amide are diazotized in a hydrochloric acid solution in the usual way and the diazo solution is added in portions at room temperature to 10 parts of copper (I) chloride in 30 parts by volume of concentrated hydrochloric acid .

   When the addition is complete, the mixture is heated to 50-60 for a further 1/4 hour, then allowed to cool and the 4-chloro-benzenesulfone-N-dimethylamide is extracted with ether. After the ether has evaporated, a brown oil remains, which distills in a high vacuum under a pressure of 0.05 mm at 140 and solidifies in the cold. It forms colorless crystals with a melting point of 80.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines 4-Chlor- benzolsulfonamides, dadurch gekennzeichnet, dass man 4-Amino-benzolsulfon-N-dimethyl- amid diazotiert und die Diazogruppe mit gupfer(I)-chlorid und Salzsäure durch Chlor ersetzt. Die entstandene neue Ver bindung, das 4-Chlor-benzolsulfon-N-di- methyl-amid, bildet farblose Kristalle vom Schmelzpunkt 80 und siedet unter einem Druck von 0,05 mm bei 140 . PATENT CLAIM: Process for the preparation of a 4-chlorobenzenesulfonamide, characterized in that 4-amino-benzenesulfon-N-dimethylamide is diazotized and the diazo group is replaced with copper (I) chloride and hydrochloric acid by chlorine. The resulting new compound, 4-chloro-benzenesulphone-N-dimethyl-amide, forms colorless crystals with a melting point of 80 and boils at 140 under a pressure of 0.05 mm.
CH246983D 1945-06-28 1945-06-28 Process for the preparation of a 4-chloro-benzenesulfonamide. CH246983A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH246983T 1945-06-28

Publications (1)

Publication Number Publication Date
CH246983A true CH246983A (en) 1947-02-15

Family

ID=4465914

Family Applications (1)

Application Number Title Priority Date Filing Date
CH246983D CH246983A (en) 1945-06-28 1945-06-28 Process for the preparation of a 4-chloro-benzenesulfonamide.

Country Status (1)

Country Link
CH (1) CH246983A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005090296A3 (en) * 2004-03-11 2005-11-24 Elan Pharm Inc N-substituted benzene sulfonamides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005090296A3 (en) * 2004-03-11 2005-11-24 Elan Pharm Inc N-substituted benzene sulfonamides
US8193389B2 (en) 2004-03-11 2012-06-05 Elan Pharmaceuticals, Inc. N-substituted benzene sulfonamides

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