CH215296A - Process for the production of a urea derivative. - Google Patents

Process for the production of a urea derivative.

Info

Publication number
CH215296A
CH215296A CH215296DA CH215296A CH 215296 A CH215296 A CH 215296A CH 215296D A CH215296D A CH 215296DA CH 215296 A CH215296 A CH 215296A
Authority
CH
Switzerland
Prior art keywords
sep
urea derivative
production
reacted
derivative
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 CH215296A publication Critical patent/CH215296A/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
    • C07C309/45—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

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       3,4-Dichlorphenylcarbaminsäure    und dieses  mit     1-Amino-3,4-d@ichlorbenzol-6-sulfonsäure     umsetzt. Das neue     Harnstoffderivat    bildet als       Natriumsalz    ein helles, in heissem Wasser  lösliches Pulver und eignet sich als Motten  schutzmittel.  



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



  b)     '/2a        Mol.    der     1-Amino-3,4-dichlorben-          zol-6-sulfonsäure    wird in trockenem     Pyridin     gelöst und unter Rühren bei     10=.l5      C       portionenweise    mit     '/"        Mol.        3,4-Dichlorphe-          nylcarbaminsäurechlorid    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 1     Liter        heissem    Wasser,     filtriert    die  heisse Lösung, aus welcher sich das Reak  tionsprodukt beim Erkalten kristallinisch ab  scheidet. Man erhält es nach dem Absaugen,  Waschen mit Wasser, Trocknen und Mahlen  als helles, in heissem Wasser lösliches Pulver.  
EMI0001.0037     
  
    Analyse:
<tb>  gefunden <SEP> Cl <SEP> = <SEP> 31,67 <SEP> % <SEP> S <SEP> = <SEP> 7,0,6
<tb>  berechnet <SEP> Cl <SEP> = <SEP> 31,50% <SEP> S <SEP> = <SEP> 7,08



  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
EMI0001.0002
    characterized in that 3, 4-dichloroaniline is reacted with phosgene to form a derivative of 3,4-dichlorophenylcarbamic acid and this is reacted with 1-amino-3,4-dichlorobenzene-6-sulfonic acid. As a sodium salt, the new urea derivative forms a pale powder that is soluble in 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 containing 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) '/ 2a mol. of the 1-amino-3,4-dichlorobenzene-6-sulfonic acid is dissolved in dry pyridine and, while stirring at 10 = .15 C, with' / "mol. 3,4-dichlorophe- The mixture is then stirred at room temperature until no more free amino groups 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 1 liter of hot water, and the hot solution is filtered, from which the reaction product separates in crystalline form on cooling. It is obtained after filtering off with suction, washing with water, drying and grinding as a light-colored powder which is soluble in hot water.
EMI0001.0037
  
    Analysis:
<tb> found <SEP> Cl <SEP> = <SEP> 31.67 <SEP>% <SEP> S <SEP> = <SEP> 7,0,6
<tb> calculates <SEP> Cl <SEP> = <SEP> 31.50% <SEP> S <SEP> = <SEP> 7.08

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Harn stoffderivates. der Formel EMI0002.0002 dadurch gekennzeichnet, dass man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und dieses mit 1-Amino-3,4-dichlorbenzol-6-sulfonsäure umsetzt. Das neue Harnstoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Motten- schutzmittel. PATENT CLAIM: Process for the production of a urea derivative. the formula EMI0002.0002 characterized in that 3,4-dichloroaniline is reacted with phosgene to form a derivative of 3,4-dichlorophenylcarbamic acid and this is reacted with 1-amino-3,4-dichlorobenzene-6-sulfonic acid. 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.
CH215296D 1938-06-16 1938-06-16 Process for the production of a urea derivative. CH215296A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH212408T 1938-06-16
CH215296T 1938-06-16

Publications (1)

Publication Number Publication Date
CH215296A true CH215296A (en) 1941-06-15

Family

ID=25725176

Family Applications (1)

Application Number Title Priority Date Filing Date
CH215296D CH215296A (en) 1938-06-16 1938-06-16 Process for the production of a urea derivative.

Country Status (1)

Country Link
CH (1) CH215296A (en)

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