CH215304A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215304A
CH215304A CH215304DA CH215304A CH 215304 A CH215304 A CH 215304A CH 215304D A CH215304D A CH 215304DA CH 215304 A CH215304 A CH 215304A
Authority
CH
Switzerland
Prior art keywords
urea derivative
production
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
Application filed by Geigy Ag J R filed Critical Geigy Ag J R
Publication of CH215304A publication Critical patent/CH215304A/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
    • C07C309/01—Sulfonic acids
    • C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
    • C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     Harnstoffderivates.       Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Harn  stoffderivates der Formel  
EMI0001.0002     
         dadumch    gekennzeichnet, dass man     3,4-Di-          chloranilin    mit     Phosgen    zu einem Derivat der       3,4-Dichlorphenylcarbaminsäure    und dieses  mit     4'-Amino-2'-sulfo-phenyl-4-chlorbenzyl-          ä.ther    umsetzt. Das neue     Harnstoffderivat     bildet als     Natriumsalz    ein helles, in heissem  Wasser lösliches Pulver und eignet sich als  Mottenschutzmittel.  



  <I>Beispiel:</I>  a) In 500 Teile     Essigester,    welche 135  Teile     Phosgen    enthalten, wird eine Lösung  von 162 Teilen     3,4-Dichloranilin    in 1000 Tei  len Essigester langsam eingetropft unter  gleichzeitigem Durchleiten eines     Phosgen-          stromes.    Nach Beendigung der Reaktion wird    das Lösungsmittel in der Wärme     abdestil-          liert,    wobei das, gebildete     3,4-Dichlorphenyl-          carbaminsäurechlorid    unter     Salzsäureabspal-          tung    in das     3,4-Dichlorph-enylisocyanat    über  geht.

    



  b)     '/ZO        Mol.        4'-Amino-2'-sulfo-phenyl-4-          chlorbenzyläther    wird in trockenem     Pyridin     gelöst und unter     Rühren    bei 10-15   C     por-          tionenweise    mit     1/2a    Mal.     3,4-Diehlorphenyl-          isocyanat    versetzt.     Dann    wird bei Raum  temperatur weitergerührt, bis     keine    freie       Aminogruppe    mehr nachweisbar ist.

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



  Process for the production of a urea derivative. The present patent relates to a process for the preparation of a urea derivative of the formula
EMI0001.0002
         dadumch that one reacts 3,4-dichloroaniline with phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this with 4'-amino-2'-sulfophenyl-4-chlorobenzyl ether. As a sodium salt, the new urea derivative forms a light-colored powder that is soluble in hot water and is suitable as a moth repellent.



  <I> Example: </I> a) A solution of 162 parts of 3,4-dichloroaniline in 1000 parts of ethyl acetate is slowly added dropwise to 500 parts of ethyl acetate containing 135 parts of phosgene while a phosgene stream is passed through at the same time. After the reaction has ended, the solvent is distilled off in the heat, the 3,4-dichlorophenylcarbamic acid chloride formed converting into the 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.

    



  b) '/ 10 mol. 4'-Amino-2'-sulfo-phenyl-4-chlorobenzyl ether is dissolved in dry pyridine and, with stirring at 10-15 ° C., in portions 1/2 times. 3,4-Diehlophenyl- isocyanate added. Stirring is then continued at room temperature until free amino groups can no longer be detected.

   Soda solution is then added until the 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 the addition of sodium chloride and, after separation, drying and grinding, it is obtained as a pale powder which is soluble in hot water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn stoffderivates der Formel EMI0002.0003 dadurch gekennzeichnet, dass man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und dieses mit 4'-Amino-2'-sulfo-phenyl-4-chlorbenzyl- äther umsetzt. Das neue Harnstoffderivat 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 EMI0002.0003 characterized in that 3,4-dichloroaniline is reacted with phosgene to give a derivative of 3,4-dichlorophenylcarbamic acid and this is reacted with 4'-amino-2'-sulfophenyl-4-chlorobenzyl ether. As a sodium salt, the new urea derivative forms a light-colored powder that is soluble in hot water and is suitable as a moth repellent.
CH215304D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215304A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215304T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215304A true CH215304A (en) 1941-06-15

Family

ID=25725184

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215304D CH215304A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215304A (en)

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