CH215293A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215293A CH215293A CH215293DA CH215293A CH 215293 A CH215293 A CH 215293A CH 215293D A CH215293D A CH 215293DA CH 215293 A CH215293 A CH 215293A
- Authority
- CH
- Switzerland
- Prior art keywords
- production
- urea derivative
- derivative
- hot water
- phosgene
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 150000003672 ureas Chemical class 0.000 title claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- VTAQLGRULYHNQX-UHFFFAOYSA-N (3,4-dichlorophenyl)carbamic acid Chemical class OC(=O)NC1=CC=C(Cl)C(Cl)=C1 VTAQLGRULYHNQX-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-Dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 210000002700 Urine Anatomy 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
Description
'Verfahren zur Herstellung eines Harnstoffderivates. Gegenstand des. vorliegenden Patentes ist ein stoffderivates dem Formel
EMI0001.0006
dadurch gekennzeichnet, dass man 3,4-Dichlor- anilin mit Phosgen zu einem Derivat der 3,4- Dichdo@rphenylcarbaminsäure und dieses mit 2-Amino-4,4'-dich@or-5'-methyl-1,1'-diphenyl- äther-2'-sulfonsäure umsetzt.
Das neue ]Elarn- stoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Mottenschutzmittel.
Beispiel: a) In 500 Teilen Essigester, welche 135 Teile Phosgen enthalten, wird eine Lösung Verfahren zur Herstellung eines Harn- von 162 Teilen 3,4-Dichloranilin in 1000 Teilen Essigester langsam eingetropft, unter gleichzeitigem Durchleiten eines Phosgen- stromes. Nach Beendigung der Reaktion wird das Lösungsmittel in der Wärme abdesfilliert, wobei das gebildete 3,
4-Dichlo#rphenylcarb- aminsäureehlorid unter Salzsäureabspaltung in das 3,4-Dichlorphenylisocyanat vom Kp." 125-130' und F. 45-46' übergeht.
b) '/2o Mol. der 2-Amino,-4,4'-diehlo@r-5'- methyl-1,1'-diphenyläther-2'-sulfonsäure wird in trockenem Pyridin gelöst und unter Rüh- ren bei 10 bis<B>15'</B> C portionenweise mit 'J.-, Mol. 3,4-Diehlorphenylisocyanat 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. Trock nen 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 substance derivative of the formula
EMI0001.0006
characterized in that 3,4-dichloro-aniline with phosgene to a derivative of 3,4-Dichdo @ rphenylcarbamic acid and this with 2-amino-4,4'-dich @ or-5'-methyl-1,1 ' -diphenyl ether-2'-sulfonic acid converts.
As a sodium salt, the new] elarnoff 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 containing 135 parts of phosgene, a solution for the production of a urine of 162 parts of 3,4-dichloroaniline in 1000 parts of ethyl acetate is slowly added dropwise, while a phosgene stream is passed through at the same time. After completion of the reaction, the solvent is distilled off in the heat, whereby the 3 formed
4-Dichlorophenylcarbamic acid chloride is converted into the 3,4-dichlorophenyl isocyanate of bp 125-130 'and 45-46' with elimination of hydrochloric acid.
b) 1/2 mol. of 2-amino, -4,4'-diehlo @ r-5'-methyl-1,1'-diphenyl ether-2'-sulfonic acid is dissolved in dry pyridine and stirred at 10 Up to <B> 15 '</B> C,' J.-, Mol. 3,4-Diehlophenylisocyanat are added in portions. The mixture is then further stirred 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 adding sodium chloride and is obtained after separation. Drying and grinding as a pale powder that is soluble in hot water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH212408T | 1938-06-16 | ||
| CH215293T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215293A true CH215293A (en) | 1941-06-15 |
Family
ID=25725173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215293D CH215293A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215293A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0765305A1 (en) * | 1994-06-02 | 1997-04-02 | Smithkline Beecham Corporation | Anti-inflammatory compounds |
-
1938
- 1938-06-16 CH CH215293D patent/CH215293A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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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