CH212780A - Process for the preparation of an aminoarylsulfonic acid derivative. - Google Patents

Process for the preparation of an aminoarylsulfonic acid derivative.

Info

Publication number
CH212780A
CH212780A CH212780DA CH212780A CH 212780 A CH212780 A CH 212780A CH 212780D A CH212780D A CH 212780DA CH 212780 A CH212780 A CH 212780A
Authority
CH
Switzerland
Prior art keywords
preparation
acid derivative
dichloro
acid
diphenylsulfide
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 CH212780A publication Critical patent/CH212780A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton

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

Description

  

  Verfahren zur Darstellung eines     Aminoarylsulfonsäurederivates.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Darstellung eines     Amino-          arylsulfonsäurederivates,    dadurch gekenn  zeichnet, dass man     4-Amino-4',5'-dichlor-1,1'-          diphenylsulfid-2-sulfonsäure    mit Palmkern  fettsäurechlorid umsetzt.  



  Die neue     Verbindung,    die     4-Lauroyl-          amino    -4',5'-     dichlor-1,1'-diphenylsulf        id-2-sul-          fonsäure,    bildet als     Natriumsalz    eine     dunkle     Paste und eignet sich als Mottenschutzmittel  und als Netzmittel.  



  <I>Beispiel:</I>  25 Teile     4-Amino,4',5'-dichlor-1,1'-di-          phenylsulfid-2-sulfonsäure        (70%),        gewonnen     durch Kondensation von 3,4 -     Dichlorthio-          phenol    mit     p-Chlornitrobenzolsulfonsäure    und  nachfolgende     Reduktion,    werden in 200  Teilen trockenem     Pyridin    suspendiert, bei 20  bis 35   C 15 Teile     Palmkernfettsäurechlorid          zugetropft    und so lange gerührt, bis in einer  Probe     keine    freie Aminosäure mehr nachweis  bar ist.

       Hierauf    wird mit Soda     phenol-          pUthaleinalkalisch    gestellt, das     Pyridin    mit    Wasserdampf abgeblasen und die zurück  bleibende     Lösung        nach,    dem Erkalten mit  Salzsäure angesäuert.

   Die ausgefällte     4-          Lauroylamino    - 4'. 5' -     dichlor-1,1'-        diphenylsul-          fid-2-sulfonsäure    wird mit     Petroläther    ge  waschen, wobei     gegebenenfalls    vorhandene,  überschüssige     Palmkernfettsäure    vollständig  entfernt wird. Das Kondensationsprodukt  wird in üblicher Weise in das     Natriumsalz     übergeführt. Man erhält eine     dunkle    Paste,  die in Wasser löslich ist.



  Process for the preparation of an aminoarylsulfonic acid derivative. The subject of the present patent is a process for the preparation of an aminoaryl sulfonic acid derivative, characterized in that 4-amino-4 ', 5'-dichloro-1,1'-diphenylsulfide-2-sulfonic acid is reacted with palm kernel fatty acid chloride.



  The new compound, 4-lauroylamino -4 ', 5'-dichloro-1,1'-diphenylsulfid-2-sulphonic acid, forms a dark paste as a sodium salt and is suitable as a moth repellent and as a wetting agent.



  <I> Example: </I> 25 parts of 4-amino, 4 ', 5'-dichloro-1,1'-diphenylsulfide-2-sulfonic acid (70%), obtained by condensation of 3,4 - dichlorothio- phenol with p-chloronitrobenzenesulfonic acid and subsequent reduction are suspended in 200 parts of dry pyridine, 15 parts of palm kernel fatty acid chloride are added dropwise at 20 to 35 ° C. and the mixture is stirred until no free amino acid can be detected in a sample.

       Then phenol-puthalein-alkaline is made with soda, the pyridine is blown off with steam and the remaining solution is acidified with hydrochloric acid after cooling.

   The precipitated 4-lauroylamino - 4 '. 5 '- dichloro-1,1'-diphenylsulphide-2-sulphonic acid is washed with petroleum ether, any excess palm kernel fatty acid that may be present being completely removed. The condensation product is converted into the sodium salt in the usual way. A dark paste is obtained which is soluble in water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Amino- arylsulfonsäurederivates, dadurch gekenn zeichnet, dass man 4-Amino-4'-5'-dichlor-1,1'- diphenylsulfid-2-sulfonsäure mit Palmkern fettsäurechlorid umsetzt. Die neue Verbindung, die 4 - Lauroyl- amino -4', 5'- dichlor-1,1'-diphenylsulfid-2-sul- fonsäure, bildet als Natriumsalz eine dunkle Paste und eignet sich als Mottenschutzmittel und als Netzmittel. PATENT CLAIM: Process for the preparation of an aminoaryl sulfonic acid derivative, characterized in that 4-amino-4'-5'-dichloro-1,1'-diphenylsulfide-2-sulfonic acid is reacted with palm kernel fatty acid chloride. The new compound, 4 - lauroylamino -4 ', 5'-dichloro-1,1'-diphenylsulfide-2-sulphonic acid, forms a dark paste as a sodium salt and is suitable as a moth repellent and as a wetting agent.
CH212780D 1938-12-24 1938-12-24 Process for the preparation of an aminoarylsulfonic acid derivative. CH212780A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH210200T 1938-12-24
CH212780T 1938-12-24

Publications (1)

Publication Number Publication Date
CH212780A true CH212780A (en) 1940-12-15

Family

ID=25724789

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212780D CH212780A (en) 1938-12-24 1938-12-24 Process for the preparation of an aminoarylsulfonic acid derivative.

Country Status (1)

Country Link
CH (1) CH212780A (en)

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