CH215300A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215300A
CH215300A CH215300DA CH215300A CH 215300 A CH215300 A CH 215300A CH 215300D A CH215300D A CH 215300DA CH 215300 A CH215300 A CH 215300A
Authority
CH
Switzerland
Prior art keywords
production
derivative
urea derivative
phosgene
hot water
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 CH215300A publication Critical patent/CH215300A/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     Harnstoffderivates.       Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines     Harn-          stoffderi%,ates    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',5'-trichtor-1,1'-diphenyl-          äther-2'-sulfonsäure    umsetzt.

   Das neue Harn  stoffderivat bildet als     Natriumsalz    ein helles,  in heissem 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<B>162</B> 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)     %O        Mol.    der     2-Amino-4,4',5'-trichlor-          1,1'-diphenyläther-2!-sulfonsäure    wird in  trockenem     Pyridin    gelöst und unter Rühren  bei<B>10-1510</B> C     portionenweise        mit        '/2o        Mol.          3,4-Dichlorphenylcarbaminsäurechlorid    ver  setzt. Dann wird bei Raumtemperatur      weitergerührt, bis keine freie     Aminobruppe     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     \Nasser,          filtriert    die Lösung, fällt das Reaktions  produkt durch Zugabe von Kochsalz als    graues Harz aus und erhält es nach dem Ab  trennen, Trocknen und Mahlen als helles, in  heissem Wasser     lösliches    Pulver.



  Process for the production of a urea derivative. The subject of the present patent is a process for the production of a urea deri%, ate 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 ', 5'-trichtor-1,1'-diphenyl-ether-2 '-sulfonic acid converts.

   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.



  <I> Example: </I> a) A solution of <B> 162 </B> 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 at the same time Passing through a phosgene stream. 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)% O mol. of the 2-amino-4,4 ', 5'-trichloro-1,1'-diphenyl ether-2! -sulfonic acid is dissolved in dry pyridine and stirred at <B> 10-1510 </ B > C in portions with 1/2 mol. 3,4-dichlorophenylcarbamic acid chloride sets. Stirring is then continued at room temperature until free amino groups can no longer be detected. Transferred to this. one with soda solution until the alkaline reaction and blows the pyridine with.

   Water vapor. 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 separating, drying and grinding, it is obtained as a pale powder that is soluble in hot water.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Herstellung eines Harn stoffderivates der Formel EMI0002.0007 dadurch gekennzeichnet, dass man 3,4-Di- chlora.nilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und dieses mit 9-Amino-4,4',5'-trichlor-l,l.'-diphenyl- äther-?'-sulfonsäure urnse-tzt. Las neue Harti- sfoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Mottenschutzmittel. <B> PATENT CLAIM: </B> Process for the production of a urea derivative of the formula EMI0002.0007 characterized in that 3,4-dichlora.niline with phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this with 9-amino-4,4 ', 5'-trichloro-l, l .'-diphenyl- ether -? '- sulphonic acid has an effect. The new Hartisfoff derivative forms a pale powder, soluble in hot water, as a sodium salt and is suitable as a moth repellent.
CH215300D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215300A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215300T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215300A true CH215300A (en) 1941-06-15

Family

ID=25725180

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215300D CH215300A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215300A (en)

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