CH215315A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215315A
CH215315A CH215315DA CH215315A CH 215315 A CH215315 A CH 215315A CH 215315D A CH215315D A CH 215315DA CH 215315 A CH215315 A CH 215315A
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 CH215315A publication Critical patent/CH215315A/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
    • C07C309/45—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

Description

  

  Verfahren zur Herstellung eines     Harnstoffderivates.       Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Harn  stoffderivates der Formel  
EMI0001.0002     
    dadurch     gekennzeichnet,    dass man     3,4-Di-          chloranilin    mit     Phosgen    zu einem Derivat  der     3,4-Dichlorphenylcarbaminsäure    und die  ses mit     4-Amino-3',4'-dichlor-1,1'-diphenyl-          äther-2-sulfonsäure    umsetzt.

   Das neue Harn  stoff     derivat    bildet     als        Natriumsalz    ein     helles,     in heissem Wasser lösliches Pulver     und    eig  net sich als     Mottenschutzmittel.     



       Beispiel:          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-Diehlorphenylisocyanat    über  geht.  



  b)     '/2o        Mol.    der     4-Amino-3',4f-dichlor@-          1,1'-diphenyläther-2-sulfonsäure    wird in  trockenem     Pyridin    gelöst und unter Rühren  bei 10-15   C     portionenweise    mit     '/ZU        Mol.          3,4-Dichlorphenylisocyanat    versetzt. Dann       wird    bei     Raumtemperatur        weitergerührt,    bis  keine freie     Aminogruppe    mehr nachweisbar      ist.

   Hierauf versetzt man mit     Sodalösung    bis  zur alkalischen Reaktion und bläst das     Py-          ridin    mit Wasserdampf ab. Den Rückstand  löst man     in    heissem Wasser, filtriert die Lö  sung, fällt das Reaktionsprodukt durch Zu  gabe von Kochsalz als graues Harz aus und    erhält es nach dem Abtrennen, Trocknen und  Mahlen als helles, in heissem Wasser lös  liches 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
    characterized in that 3,4-dichloroaniline with phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this ses with 4-amino-3 ', 4'-dichloro-1,1'-diphenyl ether-2- sulfonic acid converts.

   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.



       Example: 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, which contain 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, with the 3 formed

  4-dichlorophenylcarbamic acid chloride is converted into the 3,4-diehlophenyl isocyanate with elimination of hydrochloric acid.



  b) '/ 2o mol. of 4-Amino-3', 4f-dichloro @ -1,1'-diphenylether-2-sulfonic acid is dissolved in dry pyridine and stirred in portions at 10-15 C with '/ ZU mol. 3,4-dichlorophenyl isocyanate added. Stirring is then continued at room temperature until free amino groups can no longer be detected.

   Soda solution is then added until an alkaline reaction is obtained 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 obtained after separation, drying and grinding as a pale powder that is soluble in hot water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn stoffderivates der Formel EMI0002.0006 dadurch gekennzeichnet, dass man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylearbaminsäure und die ses mit 4-Amino-3',4'-dichlor-1,1'-diphenyl- äther-2-sulfonsäure umsetzt. Das neue Harn- stoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eig net sich als Mottenschutzmittel. PATENT CLAIM: Process for the production of a urea derivative of the formula EMI0002.0006 characterized in that 3,4-dichloroaniline with phosgene to a derivative of 3,4-dichlorophenylearbamic acid and this ses with 4-amino-3 ', 4'-dichloro-1,1'-diphenyl ether-2- sulfonic acid converts. 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.
CH215315D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215315A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215315T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215315A true CH215315A (en) 1941-06-15

Family

ID=25725195

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215315D CH215315A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215315A (en)

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