CH215299A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215299A
CH215299A CH215299DA CH215299A CH 215299 A CH215299 A CH 215299A CH 215299D A CH215299D A CH 215299DA CH 215299 A CH215299 A CH 215299A
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 CH215299A publication Critical patent/CH215299A/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 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       a,4-Dichlorphenylearbaminsäure    und dieses  mit     4-Amino-4'-tert:amyl-1,1'-.diphenyläther-          2-sulfonsäure    umsetzt. Das neue Harnstoff  derivat bildet als     Natriumsalz    ein helles, in  heissem Wasser ziemlich     schwerlösliches     Pulver und eignet sich als Mottenschutz  mittel.  



       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 im Vakuum bei 30   ab  destilliert, wobei das gebildete     3,4-Dichlor-          phenylcarbaminsäurechlorid    als helles Pulver  zurückbleibt.  



  b)     i/20        1VIol.    der     4-Amino-4'-tert.amyl-          1,1'    -     diphenyläther    -     2,-        suIfonsäure        wird    in  trockenem     Pyridin    gelöst und unter Rühren  bei<B>10-151</B> C     portionenweise    mit     i/20        Mol.          3,4-Dichlorphenylcarbaminsäurechlorid    ver  setzt. Dann wird bei     Raumtemperatur    weiter  gerührt, 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 Reaktions  produkt durch Zugabe von Kochsalz als  graues Harz aus und erhält es nach dem  Abtrennen, Trocknen und Mahlen als helles,    in heissem Wasser ziemlich     schwerlösliches     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 one 3,4-dichloroaniline with. Phosgene to a derivative of α, 4-dichlorophenylearbamic acid and this reacts with 4-amino-4'-tert: amyl-1,1 '-. Diphenyl ether-2-sulfonic acid. As a sodium salt, the new urea derivative forms a light-colored powder that is not very 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 vacuo at 30, the 3,4-dichlorophenylcarbamic acid chloride formed remaining as a pale powder.



  b) i / 20 1Viol. the 4-amino-4'-tert-amyl-1,1'-diphenyl ether-2, -sulfonic acid is dissolved in dry pyridine and mixed in portions at 10-151 C with 1/20 mol. 3,4-dichlorophenylcarbamic acid chloride sets ver. 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 precipitates as a gray resin by adding sodium chloride and, after separation, drying and grinding, it is obtained as a pale powder that is rather poorly soluble in hot water.

Claims (1)

PATENTANSPRUCH: erfahren zur Herstellung eines Harn stoffderivates der Formel EMI0002.0004 dadurch gekennzeichnet, dass man 3.4-11i- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und dieses mit 4-Amino-4'-tert.amvl-l,l'-diphenyläther- ?-sulfonsäure umsetzt. PATENT CLAIM: experienced in the production of a urea derivative of the formula EMI0002.0004 characterized in that 3.4-11i-chloroaniline is reacted with phosgene to form a derivative of 3,4-dichlorophenylcarbamic acid and this with 4-amino-4'-tert.amvl-l, l'-diphenyl ether? -sulfonic acid. Das neue Harnstoff- derivat bildet als Natriumsalz ein helles, in heissem Wasser ziemlich schwerlösliches Pulver und eignet sich als 11lottensehutz- rnittel. As a sodium salt, the new urea derivative forms a light-colored powder that is rather poorly soluble in hot water and is suitable as a detergent for lotion.
CH215299D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215299A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215299T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215299A true CH215299A (en) 1941-06-15

Family

ID=25725179

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215299D CH215299A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215299A (en)

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