CH215328A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215328A
CH215328A CH215328DA CH215328A CH 215328 A CH215328 A CH 215328A CH 215328D A CH215328D A CH 215328DA CH 215328 A CH215328 A CH 215328A
Authority
CH
Switzerland
Prior art keywords
production
urea derivative
derivative
phosgene
acid
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 CH215328A publication Critical patent/CH215328A/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     Harnstoifderivates.       Gegenstand des vorliegenden Patentes ist ein Verfahren zur     Herstellung        eines    Harn  stoffderivates der Formel  
EMI0001.0004     
    dadurch gekennzeichnet,     dass    man     3,4-Di-          chloranilin    mit     Phosgen    zu einem Derivat der       3,4-Dichlorphenylcarbaminsäure    und dieses  mit     2-Amino-4,4'-dichl-or-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.  



       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-Dichlorphenylisocyanat        über-          (reht.     



  b)     @/@o        @ol.    der     2-Amino-4,4'-dichlor-1,1'-          diphenyläther-2'-sulfonGäure    wird in trocke  nem     Pyridin    gelöst und     unter    Rühren bei  10-15   C     portionenweise    mit     %O        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     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 warmem Wasser lösliches  Pulver.



  Process for the production of a urea derivative. The subject of the present patent is a process for the preparation of a urea derivative of the formula
EMI0001.0004
    characterized in that 3,4-dichloroaniline with phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this with 2-amino-4,4'-dichloro-1,1'-diphenylether-2'-sulfonic acid implements.

   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.



       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 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.



  b) @ / @ o @ol. the 2-amino-4,4'-dichloro-1,1'-diphenylether-2'-sulfonic acid is dissolved in dry pyridine and added in portions at 10-15 ° C. with% O mol. 3,4 dichlorophenyl isocyanate. 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 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 EMI0002.0005 dadurch gekennzeichnet, dass man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und dieses mit ?-Amino-4,4'-dichlor-1,1'-diphenyläther- 2'-sulfonsäure umsetzt. Das neue Harnsfioff- derivat bildet ah, Natriumsalz ein helles, in warmem Wasser lösliches Pulver und eignet sich als Mottenschutzmittel. PATENT CLAIM: Process for the production of a urea derivative of the formula EMI0002.0005 characterized in that 3,4-dichloroaniline is reacted with phosgene to give a derivative of 3,4-dichlorophenylcarbamic acid and this with? -amino-4,4'-dichloro-1,1'-diphenyl ether-2'-sulfonic acid. The new urine-based derivative forms ah, sodium salt, a light-colored powder that is soluble in warm water and is suitable as a moth repellent.
CH215328D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215328A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215328T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215328A true CH215328A (en) 1941-06-15

Family

ID=25725208

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215328D CH215328A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215328A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2715643A (en) * 1950-12-26 1955-08-16 Variapat Ag Process for preparing n-[2'-(4'-chloro-2"-sulfophenoxy)-5'-chlorophenyl]-n'-[3, 4-dichlorophenyl]-urea
DE1031780B (en) * 1954-04-16 1958-06-12 Monsanto Chemicals Process for the preparation of halogenated carbanilides
EP0765305A1 (en) * 1994-06-02 1997-04-02 Smithkline Beecham Corporation Anti-inflammatory compounds

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2715643A (en) * 1950-12-26 1955-08-16 Variapat Ag Process for preparing n-[2'-(4'-chloro-2"-sulfophenoxy)-5'-chlorophenyl]-n'-[3, 4-dichlorophenyl]-urea
DE1031780B (en) * 1954-04-16 1958-06-12 Monsanto Chemicals Process for the preparation of halogenated carbanilides
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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