CH215298A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215298A
CH215298A CH215298DA CH215298A CH 215298 A CH215298 A CH 215298A CH 215298D A CH215298D A CH 215298DA CH 215298 A CH215298 A CH 215298A
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 CH215298A publication Critical patent/CH215298A/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

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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     Harnstoffderioates.            Gegenstand    des vorliegenden Patentes     ist    ein Verfahren zur Herstellung eines Harn  stoffderivates der Formel  
EMI0001.0004     
    dadurch gekennzeichnet, dass man     3,4-Di-          ehloranilin    mit     Phosgen    zu einem Derivat der       ;3,4-Dichlorphenylcarbaminsäure    und dieses       rnit        4-Amino-2,4'-dich@or-3',5'-dimethyl-1,1'-          diphenyläther-2'-sulfonsäure    umsetzt.

   Das  neue     Ilarnstoffderivat    bildet als     Natrium-          salz    ein helles, in heissem Wasser lösliches  Pulver und eignet sich als Mottenschutz  mittel.  



  <I>Beispiel:</I>  In 500 Teile Essigester, welche 13,5  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         abdestilliert,    wobei das gebildete     3,4-Dichlor-          phenylcarbaminsäurechlorid    als helles Pulver       zurückbleibt.     



  b)     '-/"a        Mol.    der     4-Am#ino-2;,4'-diehlor-3',5'-          dimethyl    -1,1' -     diphenyläther    -     2'-        sulfonsäure     wird in trockenem     Pyridin    gelöst und unter  Rühren bei     10=15      C     portionenweise    mit       1/2o        Mol.        3,4-Dtichlorphenylearbaminsäurechlo-          rid    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     Pyridin    mit Wasserdampf ab.  Den Rückstand löst man in heissem Wasser,  filtriert die Lösung, fällt das Reaktions  produkt durch Zugabe von     Ilochsa:z    als  bräunliches Harz aus und erhält es nach dem    Abtrennen, 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 preparation of a urea derivative of the formula
EMI0001.0004
    characterized in that 3,4-dichloroaniline is mixed with phosgene to form a derivative of; 3,4-dichlorophenylcarbamic acid and this with 4-amino-2,4'-dich @ or-3 ', 5'-dimethyl-1, 1'-diphenyl ether-2'-sulfonic acid converts.

   As a sodium salt, the new ilarnea derivative forms a pale powder that is soluble in hot water and is suitable as a moth repellent.



  <I> Example: </I> 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 13.5 parts of phosgene, while a phosgene stream is passed through at the same time. When 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) '- / "a mol. of 4-Am # ino-2;, 4'-diehlor-3', 5'-dimethyl -1,1 '- diphenyl ether - 2'-sulfonic acid is dissolved in dry pyridine and under Stirring at 10 = 15 ° C. in portions with 1/2 mol of 3,4-dichlorophenylearbamic acid chloride.

   The mixture is then further stirred at room temperature until. no more free amino group can 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 out as a brownish resin by adding Ilochsa: z and, after separation, drying and grinding, it is obtained as a pale powder which is soluble in 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-Diahlorphenylcarbaminsäure und dieses mit 4-Amino-2,4'-dichlor-3',5'-dimethyl-1,1'- diphenyläther-2'-sulfonsäure umsetzt. Das neue Harnstoffderivat bildet als Natrium salz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Mottenschutz mittel. PATENT CLAIM: Process for the production of a urea derivative of the formula EMI0002.0005 characterized in that 3,4-dichloroaniline is mixed with phosgene to form a derivative of 3,4-dialophenylcarbamic acid and this with 4-amino-2,4'-dichloro-3 ', 5'-dimethyl-1,1'- diphenyl ether-2'-sulfonic acid converts. The new urea derivative, as sodium salt, forms a light powder that is soluble in hot water and is suitable as a moth repellent.
CH215298D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215298A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215298T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215298A true CH215298A (en) 1941-06-15

Family

ID=25725178

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215298D CH215298A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215298A (en)

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