CH304981A - Process for the production of a condensation product. - Google Patents

Process for the production of a condensation product.

Info

Publication number
CH304981A
CH304981A CH304981DA CH304981A CH 304981 A CH304981 A CH 304981A CH 304981D A CH304981D A CH 304981DA CH 304981 A CH304981 A CH 304981A
Authority
CH
Switzerland
Prior art keywords
condensation product
chloro
phenyl
production
trifluoromethyl
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 CH304981A publication Critical patent/CH304981A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • 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

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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 Kondensationsproduktes.



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



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



   Beispielsweise lässt man auf den aus 2  Chlor-5-trifluormethyl-phenyl-isoeyanat    und   2-      (3',      4-Dichlor-phenoxy)-5-chlor-anilin    erhaltenen   N-2-(3', 4'-Dichlor-phenoxy)-5-chlor-phe-       nyl-N'-2-chlor-5-trifluormethyl-phenyl-harn-    stoff   Schwefelsäuremonohydrat      zwischen-7      und-+-12  einwirlien.    Hierbei wird ein   Sul-      fonsäurerest    eingeführt ; naeh Neutralisation mit konz, Natronlauge entsteht   wahrschein-    lieh die Verbindung der obigen Formel.



   Statt   Schwefelsäuremonohydrat    kann man auch Oleum oder   Chlorsulfonsäure verwen-    den. Bei letzterem arbeitet man vorzugsweise in einem Lösungsmittel, wie z. B. Nitroben  zol.    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 Rühren langsam 20 g   N-2- (3', 4'-Dichlor-phenoxy)-5-chlor-phe-      nyl-N'-2-chlor-5-    (trifluormethyl)-phenyl-harnstoff eingetragen, so dass die Temperatur nicht   über + L2     steigt. Nach dem Eintragen wird noch ungefähr eine Stunde bei dieser Temperatur weitergerührt, bis eine Probe des Reaktionsgemisches in warmer verd. Lauge klar   r 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 Öl abdekantiert und der Rückstand in 3600   emS      95 igem    Wasser gelöst, mit wenig  Tierkohle filtriert und mit   220 cm3 gesättig-    ter   Kochsalzlosung ausgesalzen. Ausbeute    :   14 g.   



   Das neue Kondensationsprodukt bildet nach dem Trocknen 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 production of a condensation product of the probable formula
EMI1.1
   characterized in that N-2- (3 ', 4'-dichloro-phenoxy) -5-chloro-phenyl-N'-2-chloro-5-trifluoromethyl-phenyl-urea is treated with a sulfonating agent and the sulfonic acid formed with a sodium compound converted into the sodium salt.



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



   For example, the N-2- (3 ', 4'-dichloro-phenoxy) obtained from 2-chloro-5-trifluoromethyl-phenyl-isoeyanate and 2- (3', 4-dichlorophenoxy) -5-chloro-aniline is allowed 5-chloro-phenyl-N'-2-chloro-5-trifluoromethyl-phenyl-urea, stir in sulfuric acid monohydrate between -7 and - + - 12. A sulphonic acid residue is introduced here; After neutralization with concentrated sodium hydroxide solution, the compound of the above formula is probably formed.



   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. nitroben zol. 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, while stirring, slowly 20 g of N-2- (3 ', 4'-dichlorophenoxy) -5-chloro-phenyl-N'-2-chloro-5- (trifluoromethyl) -phenyl urea entered, so that the temperature does not rise above + L2. 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 diluted lye.



   The reaction mixture is then poured onto ice and acidified with conc. Sodium hydroxide solution made weakly alkaline, whereby the compound precipitates as an oil. The supernatant solution is decanted from the oil and the residue is dissolved in 3600 emS 95% water, filtered with a little animal charcoal and salted out with 220 cm3 of saturated sodium chloride solution. Yield: 14 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 lvahrseheinliehen Formel EMI2.1 dadurch gekennzeichnet, dass man N-2- (3', 4'- Dichlor-phenoxy)-5-chlor-phenyl-N'-2-chlor-5- trifluormethyl-phenyl-harnstoff mit einem Sulfonierungsmittel behandelt und die ent standene Sulfonsäure mit einer Natriumverbindung in das Natriumsalz überführt. PATENT CLAIM: Process for the production of a condensation product of the inherent formula EMI2.1 characterized in that N-2- (3 ', 4'-dichloro-phenoxy) -5-chloro-phenyl-N'-2-chloro-5-trifluoromethyl-phenyl-urea is treated with a sulphonating agent and the sulphonic acid formed converted into the sodium salt with a sodium compound. Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar lösliches kristallines Pulver, das als Mottenschutzmittel verwendet werden kann. The new condensation product forms a pale crystalline powder that is clearly soluble in hot water and can be used as a moth repellent.
CH304981D 1950-04-29 1950-04-29 Process for the production of a condensation product. CH304981A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH299707T 1950-04-29
CH304981T 1950-04-29

Publications (1)

Publication Number Publication Date
CH304981A true CH304981A (en) 1955-01-31

Family

ID=25734096

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304981D CH304981A (en) 1950-04-29 1950-04-29 Process for the production of a condensation product.

Country Status (1)

Country Link
CH (1) CH304981A (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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