CH215294A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215294A
CH215294A CH215294DA CH215294A CH 215294 A CH215294 A CH 215294A CH 215294D A CH215294D A CH 215294DA CH 215294 A CH215294 A CH 215294A
Authority
CH
Switzerland
Prior art keywords
urea derivative
production
derivative
reacted
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 CH215294A publication Critical patent/CH215294A/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

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  • 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  
EMI0001.0005     
    dadurch     ,gekennzeichnet,    dass man     4-Chlor-          anilin    mit     Phosgen    zu     einem    Derivat der     4-          Chl(>rphenylcarbaminsäure        und    dieses:

   mit     2-          Amino-4,4'=dichlor-1,1'-        diphenyläther-2'-sul-          fonsäure    umsetzt. Das neue     Harnstoffderivat     bildet als     Natriumsalz    ein helles, in heissem  Wasser lösliches Pulver und     eignet    sich als       Mottenschutzmittel.     



       Beispiel:     a) In 500 Teile Essigester, welche 135  Teile     Phosgen    enthalten, wird eine Lösung  von 128 Teilen     4-Chloranilin    in 1000 Teilen  Essigester langsam eingetropft, unter gleich  zeitigem Durchleiten eines     Phosgenstromes.     Nach     Beendigung    der Reaktion wird     das    Lö  sungsmittel im Vakuum bei<B>30'</B>     abdestilliert,       wobei das gebildete     4-ChlorphenylcaTbamin-          s5,urechlorid        aals    helles Pulver zurückbleibt.  



  b)     1/2o        Mol.    der     2-Amino-4,4'-dichlor-1,1'-          diphenyläther-2'-sulfonsäure    wird in trocke  nem     Pyridin    gelöst und     unter    Rühren bei  10 bis<B>15'</B> C     portionenweise    mit     1/"o        Mol.        4-          Chlorphenylcarbaminsäurechlo@rid    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 nachdem Abtrennen, Trock-           nen    und Mahlen als helles, in heissem Nasser  ziemlich     schwerläsliches    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
EMI0001.0005
    characterized in that 4-chloroaniline with phosgene to a derivative of 4-Chl (> rphenylcarbamic acid and this:

   with 2-amino-4,4 '= dichloro-1,1'-diphenyl ether-2'-sulphonic acid is reacted. 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 128 parts of 4-chloroaniline in 1000 parts of ethyl acetate is slowly added dropwise to 500 parts of ethyl acetate containing 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 vacuo at 30 ', the 4-chlorophenyl calcium chloride formed remaining as a pale powder.



  b) 1/2 mole of the 2-amino-4,4'-dichloro-1,1'-diphenylether-2'-sulfonic acid is dissolved in dry pyridine and stirred at 10 to 15 '/ B > C in portions with 1/10 mol. 4-chlorophenylcarbamic acid chloride added.

    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 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 rather difficult to dissolve in hot water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn s s toffderivates der Formel EMI0002.0007 dadurch gekennzeichnet, dass man 4-Chlor- anilin mit Phosgen zu einem Derivat der 4-- Chlorphenylcarbaminsäure und dieses mit 2 Amino-4,4'-dichlor-1,1'- diphen.yläther-2'-sul- fonsäure umsetzt. PATENT CLAIM: Process for the production of a urea derivative of the formula EMI0002.0007 characterized in that 4-chloroaniline is reacted with phosgene to form a derivative of 4- chlorophenylcarbamic acid and this is reacted with 2-amino-4,4'-dichloro-1,1'-diphenyl ether-2'-sulphonic acid. Das neue Harnstoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Mottenschutzmittel. 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.
CH215294D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215294A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215294T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215294A true CH215294A (en) 1941-06-15

Family

ID=25725174

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215294D CH215294A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215294A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0765305A4 (en) * 1994-06-02 1997-09-03 Smithkline Beecham Corp ANTI-INFLAMMATORY COMPOUNDS

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0765305A4 (en) * 1994-06-02 1997-09-03 Smithkline Beecham Corp ANTI-INFLAMMATORY COMPOUNDS

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