CH215310A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215310A
CH215310A CH215310DA CH215310A CH 215310 A CH215310 A CH 215310A CH 215310D A CH215310D A CH 215310DA CH 215310 A CH215310 A CH 215310A
Authority
CH
Switzerland
Prior art keywords
urea derivative
production
reacted
derivative
amino
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 CH215310A publication Critical patent/CH215310A/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

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

Description

  

  Verfahren zur Her Stellung 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-4'-chlor-1,1'-diphenyläther-          3-sulfonsäure    umsetzt. Das neue Harnstoff  derivat bildet als     Natriumsalz    ein helles, in  heissem Wasser lösliches Pulver und eignet  sieh 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-          earbaminsäurechlorid    unter     Salzsäureabspal-          tung    in das     3,4-Dichlorphenylisocyanat    über  geht.  



  b)     '/2o        Mol.    der     4-Amino-4'chlor-1,1'-di-          phenyläther-3-sulfonsäure,    hergestellt durch  Erhitzen des sauren Sulfates des     4-Amino-4'-          chlordiphenyläthers    wird in trockenem     Pyri-          din    gelöst     und    unter Rühren bei 10-15   C       portionenweise    mit     1/z,        Mol.    3,4 -     Diehlor-          phenylisocyanat    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     Pvridiii     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 preparation 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 is reacted with phosgene to form a derivative of 3,4-dichlorophenylcarbamic acid and this is reacted with 4-amino-4'-chloro-1,1'-diphenyl ether-3-sulfonic acid. 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) In 500 parts of ethyl acetate which contain 135 parts of phosgene, a solution of 162 parts of 3,4-dichloroaniline in 1000 parts of ethyl acetate is slowly added dropwise 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-dichlorophenylearbamic acid chloride formed converting into the 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.



  b) '/ 20 mol. of 4-Amino-4'chlor-1,1'-diphenyl ether-3-sulfonic acid, prepared by heating the acidic sulfate of 4-amino-4'-chlorodiphenyl ether in dry pyridine dissolved and, while stirring at 10-15 ° C., 1/2 mol. 3,4 - diehlorphenyl isocyanate was added in portions.

   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 achieved and the pvridiii are blown off with steam. The residue is dissolved in hot water and the solution is filtered. the reaction product precipitates as a gray resin by adding sodium chloride and, after separation, drying and grinding, it is obtained as a light-colored powder that is soluble in hot water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn stoffderivates der Formel EMI0002.0006 dadurch gekennzeichnet, dass inan 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorpheny lcarbaminsäure und die ses mit 4-Amino-4'-ehlor-1,1'-diphenyläther- 3-sulfonsäure umsetzt. Das neue Harnstoff- derivat 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 EMI0002.0006 characterized in that inan 3,4-dichloroaniline is reacted with phosgene to form a derivative of 3,4-dichlorophenyl carbamic acid and this is reacted with 4-amino-4'-chloro-1,1'-diphenylether-3-sulfonic acid. As a sodium salt, the new urea derivative forms a light powder that is soluble in hot water and is suitable as a moth repellent.
CH215310D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215310A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH215310T 1938-06-16
CH212408T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215310A true CH215310A (en) 1941-06-15

Family

ID=25725190

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215310D CH215310A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215310A (en)

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