CH215305A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215305A
CH215305A CH215305DA CH215305A CH 215305 A CH215305 A CH 215305A CH 215305D A CH215305D A CH 215305DA CH 215305 A CH215305 A CH 215305A
Authority
CH
Switzerland
Prior art keywords
urea derivative
production
derivative
acid
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 CH215305A publication Critical patent/CH215305A/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     Harnstoüderivates.       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 dieses  mit     4-Amino-4'-chlor-1,1'-diphenyläther-2'-          sulfonsäure    umsetzt. Das neue Harnstoff  derivat bildet als     Natriumsalz    ein helles, in  warmem 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  bleichzeitigem Durchleiten eines Phosgen-         stromes.    Nach Beendigung der     Reaktion    wird  .das Lösungsmittel in der Wärme     abdestil-          liert,    wobei das gebildete     3,4-Diehlorphenyl-          carbaminsäurechlorid    unter     Salzsäureabspal-          tung    in das     3@,

  4-Dichlorphenylisocyanat    über  geht.  



  b)     '/",        Mol.    der     4-Amino-4'-chlor-1,1'-          diphenyläther-2'-sulfonsäure    wird in     trok-          kenem        Pyridin    gelöst und     unter    Rühren bei  10-15   C     portionenweise    mit     %O        Mol.        3,4-          Dichlorphenylis@ocyanat    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     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         i        als        helles,        in        warmem        Nasser        lösliches     Pulver.



  Process for the production of a urinary 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 is reacted with phosgene to give a derivative of 3,4-dichlorophenylcarbamic acid and this with 4-amino-4'-chloro-1,1'-diphenyl ether-2'-sulfonic acid. As a sodium salt, the new urea derivative forms a light-colored powder that is soluble in warm 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 which contain 135 parts of phosgene while a stream of phosgene is passed through at the same time. After the reaction has ended, the solvent is distilled off in the heat, the 3,4-diehlophenylcarbamic acid chloride formed being converted into the 3 @, with elimination of hydrochloric acid.

  4-dichlorophenyl isocyanate goes over.



  b) '/ ", Mol. The 4-amino-4'-chloro-1,1'-diphenylether-2'-sulfonic acid is dissolved in dry pyridine and stirred at 10-15 C in portions with% O mol. 3,4-dichlorophenyl isocyanate is added and stirring is continued 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 the addition of sodium chloride and, after separation, drying and grinding, it is obtained as a pale powder which is soluble in warm water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn- stoffderivates der Formel EMI0002.0012 dadurch gekennzeichnet, dass man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylearbaminsäure und dieses mit 4-Amino-4'-chlor-1,1'-diphenyläther-9'- sulfonsäure umsetzt. Das neue Harnstoff- derivat bildet als Natriumsalz ein helles, in -armem 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 reacted with phosgene to give a derivative of 3,4-dichlorophenylearbamic acid and this with 4-amino-4'-chloro-1,1'-diphenyl ether-9'-sulfonic acid. As a sodium salt, the new urea derivative forms a light-colored powder that is soluble in poor water and is suitable as a moth repellent.
CH215305D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215305A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215305T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215305A true CH215305A (en) 1941-06-15

Family

ID=25725185

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215305D CH215305A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215305A (en)

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