CH215319A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215319A CH215319A CH215319DA CH215319A CH 215319 A CH215319 A CH 215319A CH 215319D A CH215319D A CH 215319DA CH 215319 A CH215319 A CH 215319A
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 3
- VTAQLGRULYHNQX-UHFFFAOYSA-N (3,4-dichlorophenyl)carbamic acid Chemical class OC(=O)NC1=CC=C(Cl)C(Cl)=C1 VTAQLGRULYHNQX-UHFFFAOYSA-N 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000000227 grinding Methods 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
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 210000002700 urine Anatomy 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
- C07C309/45—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
Landscapes
- 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 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 4-Amino-2',5'-dichlor-1,1'-diphenyläther- 2-sulfonsäure umsetzt.
Das neue Harnstoff derivat bildet als, Natriumsalz ein helles, in heissem 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 Verfahren zur Herstellung eines Harn- gleichzeitigem Durchleiten eines Phosgen- stromes. Nach Beendigung der Reaktion wird dasLösungsmittel in,derWärme abdestilliert, wobei das gebildete 3,
4-Dichlorphenylcarb- a-minsäurechlorid unter Salzsäureabspaltung in das 3,4-Dichlorphenylisocyanat übergeht.
b) 112p Mol. der 4-Amino-2',5'-@dichlor- 1,1'-diphenyläther-2-sulfonsäurewird in trok- kenem Pyridin gelöst und unter Rühren bei 10 bis<B>15'</B> C portionenweise mit 1/" Mal-, 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 Pyri- din mit Wasserdampf ab. Den Rückstand löst man in heissem Wasser, filtriert die Lö sung, fällt das Reaktionsprodukt durch Zu gabe von Kochsalz als graues Harz aus und
EMI0002.0004
dadurch gekennzeichnet, da.ss man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und dieses mit 4-Amino-2',5'-dichlor-1,1'-diphenyläther- 2-sulfonsäure umsetzt.
Das neue Harnstoff- 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 substance derivative of the formula
EMI0001.0004
characterized in that 3,4-dichloroaniline is reacted with phosgene to give a derivative of 3,4-dichlorophenylcarbamic acid and this with 4-amino-2 ', 5'-dichloro-1,1'-diphenylether-2-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.
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, using a method for producing urine while a phosgene stream is passed through. After the reaction has ended, the solvent is distilled off in the heat, whereby the 3,
4-dichlorophenylcarb-a-minic acid chloride passes into the 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.
b) 112p mol. of the 4-amino-2 ', 5' - @ dichloro-1,1'-diphenyl ether-2-sulfonic acid is dissolved in dry pyridine and stirred at 10 to 15 ' 1 / ″ Mal-, 3,4-dichlorophenyl isocyanate are added to C in portions. 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 adding sodium chloride and
EMI0002.0004
characterized in that 3,4-dichloroaniline is combined with phosgene to form a derivative of 3,4-dichlorophenylcarbamic acid and this with 4-amino-2 ', 5'-dichloro-1,1'-diphenyl ether-2-sulfonic acid implements.
The new urea 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 | ||
| CH215319T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215319A true CH215319A (en) | 1941-06-15 |
Family
ID=25725199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215319D CH215319A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215319A (en) |
-
1938
- 1938-06-16 CH CH215319D patent/CH215319A/en unknown
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