CH304980A - Process for the production of a condensation product. - Google Patents

Process for the production of a condensation product.

Info

Publication number
CH304980A
CH304980A CH304980DA CH304980A CH 304980 A CH304980 A CH 304980A CH 304980D A CH304980D A CH 304980DA CH 304980 A CH304980 A CH 304980A
Authority
CH
Switzerland
Prior art keywords
condensation product
production
chlorophenyl
dichlorophenoxy
hot water
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Variapat
Original Assignee
Ag Variapat
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 Variapat filed Critical Ag Variapat
Publication of CH304980A publication Critical patent/CH304980A/en

Links

Classifications

    • 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
    • C07C309/41—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
    • C07C309/42—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton having the sulfo groups bound to carbon atoms of non-condensed six-membered aromatic rings

Description

  

  



  Verfahren zur Herstellung eines Kondensationsproduktes.



   Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Konden  sationsproduktes    der wahrscheinlichen Formel
EMI1.1     
 dadureh gekennzeichnet, dass man N-2- (3', 4' Dichlor-phenoxy)-5-chlor-phenyl-N'-3-trifluor  methyl-4-chlor-phenyl-harnstoff    mit einem Sulfonierungsmittel behandelt und die ent  standene    Sulfonsäure mit einer Natriumverbindung in das Natriumsalz überführt.



   Als Sulfonierungsmittel kommen zum Beispiel in Frage : Oleum, konz. Schwefelsäure oder Chlorsulfonsäure.



   Beispielsweise lässt man auf den aus 3-Tri  fluormethyl-4-chlor-phenyl-isocyanat    und 2  (3', 4'-Dichlor-phenoxy)-5-chlor-anilin    erhaltenen N-2-(3',4'-Dichlor-phenoxy)-5-chlor-phenyl-N'-3-trifluormethyl-4-ehlor-phenyl-harnstoff   Schwefelsäuremonohydrat    zwischen-7 und+12¯ einwirken. Hierbei wird ein Sul  l'onsäurerest eingeführt    ; nach Neutralisation mit konz. Natronlauge entsteht   wahrschein-      lich die Verbindung    der obigen Formel.



   Statt   Schwefelsäuremonohydrat    kann man auch Oleum oder Chlorsulfonsäure verwenden. Bei letzterem arbeitet man vorzugsweise in einem Losungsmittel, wie z. B. Nitrobenzol.



  Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar lösliches Kristallpulver, das als Mottenschutzmittel verwendet werden kann.



   Beispiel :
100 g   Schwefelsäuremonohydrat    werden auf-7  gekühlt und unter R hren langsam   20    g N-2-   (3',    4'-Dichlor-phenoxy)-5-chlor-phenyl-N'-3-trifluormethyl-4-chlor-phenyl-harnstoff eingetragen, so dass die Temperatur nicht   über- (-12" steigt. Nach    dem Eintragen wird noch ungefähr eine Stunde bei dieser Temperatur weitergerührt, bis eine Probe des   Reaktionsgemisehes    in warmer verd. Lauge klar löslieh ist.



   Darauf wird das Reaktionsgemisch auf Eis gegossen. und mit konz. Natronlauge schwach alkalisch gestellt, wobei die Verbindung als öl ausfällt. Die überstehende Lösung wird vom   61    abdekantiert und der Rüekstand, in 3500   em3      95 igem    Wasser gelöst, mit wenig   Tierkohle    filtriert und mit   150    em3 gesättigter Kochsalzlosung ausgesalzen. Ausbeute :   15 g.   



   Das neue Kondensationsprodukt bildet naeh dem   Troeknen    und Mahlen ein helles, in heissem Wasser klar lösliches kristallines Pulver.



  



  Process for the production of a condensation product.



   The subject of the present patent is a process for the preparation of a condensation product of the probable formula
EMI1.1
 characterized in that N-2- (3 ', 4' dichlorophenoxy) -5-chlorophenyl-N'-3-trifluoro methyl-4-chlorophenyl urea is treated with a sulfonating agent and the sulfonic acid formed converted into the sodium salt with a sodium compound.



   Suitable sulfonating agents are, for example: oleum, conc. Sulfuric acid or chlorosulfonic acid.



   For example, the N-2- (3 ', 4'-dichloro) obtained from 3-trifluoromethyl-4-chloro-phenyl isocyanate and 2 (3', 4'-dichloro-phenoxy) -5-chloro-aniline -phenoxy) -5-chloro-phenyl-N'-3-trifluoromethyl-4-chloro-phenyl-urea sulfuric acid monohydrate between -7 and + 12¯ act. A sul l'onic acid residue is introduced here; after neutralization with conc. Sodium hydroxide is likely to form the compound of the formula above.



   Instead of sulfuric acid monohydrate, oleum or chlorosulfonic acid can also be used. In the latter one works preferably in a solvent, such as. B. nitrobenzene.



  The new condensation product forms a pale crystal powder that is clearly soluble in hot water and can be used as a moth repellent.



   Example:
100 g of sulfuric acid monohydrate are cooled to -7 and, with stirring, slowly 20 g of N-2- (3 ', 4'-dichlorophenoxy) -5-chlorophenyl-N'-3-trifluoromethyl-4-chlorophenyl- urea is added so that the temperature does not rise above (-12 ". After the addition, stirring is continued for about an hour at this temperature until a sample of the reaction mixture is clearly soluble in warm dilute lye.



   The reaction mixture is then poured onto ice. and with conc. Sodium hydroxide solution made slightly alkaline, the compound precipitating as an oil. The supernatant solution is decanted off and the residue, dissolved in 3500 cubic meters of 95% water, filtered with a little animal charcoal and salted out with 150 cubic meters of saturated sodium chloride solution. Yield: 15 g.



   After drying and grinding, the new condensation product forms a pale crystalline powder that is clearly soluble in hot water.

Claims (1)

PATENTANSPRUCH : Verfahren zur Herstellung eines Konden sationsproduktes der wahrscheinlichen Formel EMI2.1 dadurch gekennzeichnet, dass man N-2- (3', 4'- Dichlor-phenoxy)-5-chlor-phenyl-N'-3-trifluor methyl-4-ehlor-phenyl-harnstoff mit einem Sulfonierungsmittel behandelt und die entstandene Sulfonsäure mit einer Natriumver- bindung in das Natriumsalz überführt. PATENT CLAIM: Process for the preparation of a condensation product of the probable formula EMI2.1 characterized in that N-2- (3 ', 4'-dichlorophenoxy) -5-chlorophenyl-N'-3-trifluoro methyl-4-chlorophenylurea is treated with a sulfonating agent and the sulfonic acid formed converted into the sodium salt with a sodium compound. Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar lösliehes kristallines Pulver, das als Mottenschutzmittel verwendet werden kann. The new condensation product forms a pale crystalline powder that dissolves clearly in hot water and can be used as a moth repellent.
CH304980D 1950-04-29 1950-04-29 Process for the production of a condensation product. CH304980A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH299707T 1950-04-29
CH304980T 1950-04-29

Publications (1)

Publication Number Publication Date
CH304980A true CH304980A (en) 1955-01-31

Family

ID=25734095

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304980D CH304980A (en) 1950-04-29 1950-04-29 Process for the production of a condensation product.

Country Status (1)

Country Link
CH (1) CH304980A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0765305A1 (en) * 1994-06-02 1997-04-02 Smithkline Beecham Corporation Anti-inflammatory compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0765305A1 (en) * 1994-06-02 1997-04-02 Smithkline Beecham Corporation Anti-inflammatory compounds
EP0765305A4 (en) * 1994-06-02 1997-09-03 Smithkline Beecham Corp Anti-inflammatory compounds

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