CH215318A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215318A
CH215318A CH215318DA CH215318A CH 215318 A CH215318 A CH 215318A CH 215318D A CH215318D A CH 215318DA CH 215318 A CH215318 A CH 215318A
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 CH215318A publication Critical patent/CH215318A/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
    • C07C309/41—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  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     4-Amino.-2-chlor-4'-tert.amyl-1,1'-diphe-          nyläther-2'-sulfonsäure    umsetzt.

       Dass    neue       Harnstoffderivat    bildet als     Natriumsalz    ein  helles, in viel 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 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,derWärme        abdestilliert,     wobei das gebildete     3,4-Dichlorphenylcarb-          aminsäurechlorid    unter     Salzsäureabspaltung     in das     3,

  4-Dichlorphenylisocyanat    übergeht.  



  b)     1/2a        Mol.    der     4-Amino-2-chlor-4'-tert.          amyl-1,1'-diphenyläther-2'-sulfonsäure    wird  in trockenem     Pyridin    gelöst und unter Rüh  ren bei 10 bis<B>15'</B> C     portionenweise    mit       I/ZO        Mol.        3,4-Dichlorphenylisocyanat    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 nach dem Abtrennen,  Trocknen und Mahlen     als    helles, in viel hei  ssem 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 is combined with phosgene to form a derivative of 3,4-dichlorophenylcarbamic acid and this with 4-amino.-2-chloro-4'-tert.amyl-1,1'-diphe- Nylether-2'-sulfonic acid converts.

       The sodium salt of the new urea derivative forms a light powder that is soluble in a lot of hot water and is suitable as a moth repellent.



  <I> Example: </I> 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, the 3,4-dichlorophenylcarbamic acid chloride formed being converted into the 3, with elimination of hydrochloric acid.

  4-dichlorophenyl isocyanate passes over.



  b) 1 / 2a mol. of 4-amino-2-chloro-4'-tert. Amyl-1,1'-diphenylether-2'-sulfonic acid is dissolved in dry pyridine and I / ZO moles of 3,4-dichlorophenyl isocyanate are added in portions at 10 to 15 ° C. with stirring. The mixture is then further stirred at room temperature until free amino groups can no longer be detected.

   Soda solution is then added until it is alkaline; Reaction and blows off the pyridine with steam. The residue is dissolved in hot water, the solution 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 soluble in plenty of hot 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 4-Amino-2-chlor-4'-tert.amyl-1,1'-diphe- nyläther-2'-sulfonsäure umsetzt. Das neue Harnstoffderivat bildet als Natriumsalz ein 2s helles, in viel heissem 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 with phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this with 4-amino-2-chloro-4'-tert.amyl-1,1'-diphenyl ether 2'-sulfonic acid converts. As a sodium salt, the new urea derivative forms a 2s-light powder that is soluble in plenty of hot water and is suitable as a moth repellent.
CH215318D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215318A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215318T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215318A true CH215318A (en) 1941-06-15

Family

ID=25725198

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215318D CH215318A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215318A (en)

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