CH215328A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215328A CH215328A CH215328DA CH215328A CH 215328 A CH215328 A CH 215328A CH 215328D A CH215328D A CH 215328DA CH 215328 A CH215328 A CH 215328A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- urea derivative
- derivative
- phosgene
- acid
- Prior art date
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Harnstoifderivates. 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 2-Amino-4,4'-dichl-or-1,1'-diphenyläther- 2'-sulfonsäure umsetzt.
Das neue Harnstoff derivat bildet als Natriumsalz ein helles, in warmem Wasser lösliches Pulver und eignet sich als Mottenschutzmittel.
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- (reht.
b) @/@o @ol. der 2-Amino-4,4'-dichlor-1,1'- diphenyläther-2'-sulfonGäure wird in trocke nem Pyridin gelöst und unter Rühren bei 10-15 C portionenweise mit %O Mol. 3,4 Dichlorphenylisocyanat 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 Reaktionsprodukt durch Zugabe von Kochsalz als graues Harz aus und erhält es nach dem Abtrennen, Trocknen und Mahlen als helles, in warmem 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 with phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this with 2-amino-4,4'-dichloro-1,1'-diphenylether-2'-sulfonic acid implements.
As a sodium salt, the new urea derivative forms a light-colored powder that is soluble in warm water and is suitable as a moth repellent.
Example: 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, with the 3 formed
4-dichlorophenylcarbamic acid chloride is converted into 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.
b) @ / @ o @ol. the 2-amino-4,4'-dichloro-1,1'-diphenylether-2'-sulfonic acid is dissolved in dry pyridine and added in portions at 10-15 ° C. with% O mol. 3,4 dichlorophenyl isocyanate. Stirring is then continued at room temperature until free amino groups can no longer 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 is precipitated as a gray resin by the addition of sodium chloride and, after separation, drying and grinding, it is obtained as a pale powder which is soluble in warm water.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH215328T | 1938-06-16 | ||
CH212408T | 1938-06-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH215328A true CH215328A (en) | 1941-06-15 |
Family
ID=25725208
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH215328D CH215328A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH215328A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2715643A (en) * | 1950-12-26 | 1955-08-16 | Variapat Ag | Process for preparing n-[2'-(4'-chloro-2"-sulfophenoxy)-5'-chlorophenyl]-n'-[3, 4-dichlorophenyl]-urea |
DE1031780B (en) * | 1954-04-16 | 1958-06-12 | Monsanto Chemicals | Process for the preparation of halogenated carbanilides |
EP0765305A1 (en) * | 1994-06-02 | 1997-04-02 | Smithkline Beecham Corporation | Anti-inflammatory compounds |
-
1938
- 1938-06-16 CH CH215328D patent/CH215328A/en unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2715643A (en) * | 1950-12-26 | 1955-08-16 | Variapat Ag | Process for preparing n-[2'-(4'-chloro-2"-sulfophenoxy)-5'-chlorophenyl]-n'-[3, 4-dichlorophenyl]-urea |
DE1031780B (en) * | 1954-04-16 | 1958-06-12 | Monsanto Chemicals | Process for the preparation of halogenated carbanilides |
EP0765305A1 (en) * | 1994-06-02 | 1997-04-02 | Smithkline Beecham Corporation | Anti-inflammatory compounds |
EP0765305A4 (en) * | 1994-06-02 | 1997-09-03 | Smithkline Beecham Corp | Anti-inflammatory compounds |
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