CH215313A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215313A
CH215313A CH215313DA CH215313A CH 215313 A CH215313 A CH 215313A CH 215313D A CH215313D A CH 215313DA CH 215313 A CH215313 A CH 215313A
Authority
CH
Switzerland
Prior art keywords
production
urea derivative
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 CH215313A publication Critical patent/CH215313A/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  
EMI0001.0004     
    dadurch gekennzeichnet, dass man     3,4-Di-          ehloranilin    mit     Phosgen    zu einem Derivat  der     3,4-Dichlorphenylcarbaminsäure    und die  ses mit     4-Amino-2'-methyl-g        -chlor-l,l'-di-          phenyläther-2-sulfonsäure,    zu deren Herstel  lung ein chloriertes     o-gresol    verwendet wird,  umsetzt.

   Das neue     Harästoffderivat    bildet  als     Natriumsalz    ein helles, in heissem Wasser  lösliches Pulver und eignet sich als Motten  schutzmittel.  



       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-          carbaminsäurechlorid    unter     Salzsäureabspal-          tung    in das     3,4-Dichlorphenylisocyanat    über  geht.  



  b)     1/2u        Mol.        4-Amino-2'-methyl-g        -chlor-          1,1'-diphenyläther-2-sulfonsäure,    zu deren  Herstellung ein chloriertes     o-gresol    verwen  det wird, wird in     trockenem        Pyridin    gelöst       und    unter Rühren bei 10-15   C     portionen-          weise    mit     '/ZO        Mol.        3,4-Dichlorphenyliso-          cyanat        versetzt.    Dann wird bei Raumtempe  ratur weitergerührt,

       bis    keine freie     Amino-          gruppe    mehr nachweisbar ist. Hierauf ver  setzt man mit     Sodalösung    bis zur alkalischen      Reaktion und bläst das     Pyridin    mit Wasser  dampf ab. Den Rückstand löst man in heissem  Wasser,     filtriert    die Lösung, fällt das Re  aktionsprodukt 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 production of a urea derivative. The present patent relates to 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 is mixed with 4-amino-2'-methyl-g-chloro-l, l'-diphenyl ether-2 -sulfonic acid, for the production of which a chlorinated o-gresol is used.

   The sodium salt of 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. After the reaction has ended, the solvent is in the heat distilled off, whereby the 3 formed

  4-dichlorophenylcarbamic acid chloride passes into the 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.



  b) 1 / 2u mol. 4-Amino-2'-methyl-g-chloro-1,1'-diphenyl ether-2-sulfonic acid, for the preparation of which a chlorinated o-gresol is used, is dissolved in dry pyridine and under Stirring at 10-15 ° C., 1/10 mol. 3,4-dichlorophenyl isocyanate is added in portions. Then continue stirring at room temperature,

       until no more free amino groups can be detected. Then one sets ver with soda solution until an alkaline reaction and the pyridine is blown off with steam. The residue is dissolved in hot water, the solution is filtered, the reaction product is precipitated as a gray resin by adding sodium chloride and obtained as a pale resin after separation, drying and grinding. Powder soluble in hot water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn- stoffderivatc-s der Formel EMI0002.0008 dadurch gekennzeichnet, dass man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und die ses mit 4-Amino-2'-methyl-x'-chlor-1,1'-di- phenyläther-2-sulfonsäure, zu deren Herstel- lung ein chloriertes o-Kresol verwendet wird, umsetzt. PATENT CLAIM: Process for the production of a urea derivative of the formula EMI0002.0008 characterized in that 3,4-dichloroaniline with phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this ses with 4-amino-2'-methyl-x'-chloro-1,1'-diphenyl ether 2-sulfonic acid, for the production of which a chlorinated o-cresol is used. Das neue Harnstoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Motten schutzmittel. 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.
CH215313D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215313A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215313T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215313A true CH215313A (en) 1941-06-15

Family

ID=25725193

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215313D CH215313A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215313A (en)

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