CH215293A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215293A
CH215293A CH215293DA CH215293A CH 215293 A CH215293 A CH 215293A CH 215293D A CH215293D A CH 215293DA CH 215293 A CH215293 A CH 215293A
Authority
CH
Switzerland
Prior art keywords
production
urea derivative
derivative
hot water
phosgene
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
Priority claimed from CH212408T external-priority
Application filed by Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH215293A publication Critical patent/CH215293A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01Sulfonic acids
    • C07C309/28Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/41Sulfonic 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

Description

  

      'Verfahren    zur Herstellung eines     Harnstoffderivates.            Gegenstand    des. vorliegenden Patentes ist ein       stoffderivates        dem    Formel  
EMI0001.0006     
    dadurch gekennzeichnet, dass man     3,4-Dichlor-          anilin    mit     Phosgen    zu einem Derivat der     3,4-          Dichdo@rphenylcarbaminsäure    und dieses mit       2-Amino-4,4'-dich@or-5'-methyl-1,1'-diphenyl-          äther-2'-sulfonsäure    umsetzt.

   Das neue     ]Elarn-          stoffderivat    bildet als     Natriumsalz    ein helles,  in     heissem    Wasser lösliches Pulver und eignet  sich als     Mottenschutzmittel.     



       Beispiel:     a) In 500 Teilen     Essigester,    welche 135       Teile        Phosgen    enthalten, wird eine     Lösung       Verfahren zur Herstellung     eines    Harn-    von 162 Teilen     3,4-Dichloranilin    in 1000  Teilen Essigester langsam eingetropft, unter  gleichzeitigem Durchleiten eines     Phosgen-          stromes.    Nach Beendigung der Reaktion wird  das     Lösungsmittel    in der     Wärme        abdesfilliert,     wobei das gebildete     3,

  4-Dichlo#rphenylcarb-          aminsäureehlorid        unter        Salzsäureabspaltung     in das     3,4-Dichlorphenylisocyanat    vom     Kp."          125-130'    und F. 45-46' übergeht.  



  b)     '/2o        Mol.    der     2-Amino,-4,4'-diehlo@r-5'-          methyl-1,1'-diphenyläther-2'-sulfonsäure    wird  in trockenem     Pyridin    gelöst und unter Rüh-           ren    bei 10 bis<B>15'</B> C     portionenweise    mit     'J.-,          Mol.        3,4-Diehlorphenylisocyanat    versetzt.  Dann wird bei Raumtemperatur weiterge  rührt, bis keine freie     Aminogruppe    mehr  nachweisbar ist.

   Hierauf versetzt man mit       Sodalösung    bis zur alkalischen Reaktion und  bläst das     Pyridin    mit Wasserdampf ab. Den  Rückstand löst man in heissem Wasser, fil-         triert    die Lösung,     fällt    das Reaktionsprodukt  durch Zugabe von Kochsalz als graues Harz  aus und erhält es nach dem Abtrennen. Trock  nen und Mahlen als helles, in heissem Wasser  lösliches Pulver.



      '' Process for the production of a urea derivative. The subject of the present patent is a substance derivative of the formula
EMI0001.0006
    characterized in that 3,4-dichloro-aniline with phosgene to a derivative of 3,4-Dichdo @ rphenylcarbamic acid and this with 2-amino-4,4'-dich @ or-5'-methyl-1,1 ' -diphenyl ether-2'-sulfonic acid converts.

   As a sodium salt, the new] elarnoff derivative forms a light-colored powder that is soluble in hot water and is suitable as a moth repellent.



       Example: a) In 500 parts of ethyl acetate containing 135 parts of phosgene, a solution for the production of a urine of 162 parts of 3,4-dichloroaniline in 1000 parts of ethyl acetate is slowly added dropwise, while a phosgene stream is passed through at the same time. After completion of the reaction, the solvent is distilled off in the heat, whereby the 3 formed

  4-Dichlorophenylcarbamic acid chloride is converted into the 3,4-dichlorophenyl isocyanate of bp 125-130 'and 45-46' with elimination of hydrochloric acid.



  b) 1/2 mol. of 2-amino, -4,4'-diehlo @ r-5'-methyl-1,1'-diphenyl ether-2'-sulfonic acid is dissolved in dry pyridine and stirred at 10 Up to <B> 15 '</B> C,' J.-, Mol. 3,4-Diehlophenylisocyanat are added in portions. The mixture is then further stirred at room temperature until free amino groups can no longer be detected.

   Soda solution is then added until an alkaline reaction occurs and the pyridine is blown off with steam. The residue is dissolved in hot water, the solution is filtered, the reaction product is precipitated as a gray resin by adding sodium chloride and is obtained after separation. Drying and grinding as a pale powder that is soluble in hot water.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn stoff derivates der Formel EMI0002.0012 dadurch gekennzeichnet"dass man 3,4-Dichlor- anilin mit Phosgen zu einem Derivat der 3,4- Dichlorphenylcarbaminsäure und dieses mit ?-Amino-4,4'-dichlor-5'-methyl-1,1'-diphenyl- äther-2'-sulfonsäure umsetzt. Das neue Harn- Stoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Mottenschutzmittel. PATENT CLAIM: Process for the production of a urea derivative of the formula EMI0002.0012 characterized in that "3,4-dichloroaniline is mixed with phosgene to form a derivative of 3,4-dichlorophenylcarbamic acid and this with? -amino-4,4'-dichloro-5'-methyl-1,1'-diphenyl ether The new urea derivative forms a light-colored powder that is soluble in hot water and is suitable as a moth repellent.
CH215293D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215293A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215293T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215293A true CH215293A (en) 1941-06-15

Family

ID=25725173

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215293D CH215293A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215293A (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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