CH215314A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215314A CH215314A CH215314DA CH215314A CH 215314 A CH215314 A CH 215314A CH 215314D A CH215314D A CH 215314DA CH 215314 A CH215314 A CH 215314A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea derivative
- production
- derivative
- acid
- hot water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 150000003672 ureas Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 239000002253 acid Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate 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
- 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
- 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
- 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 1
- 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
- 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
- 238000002360 preparation method 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
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 Verfahren zur Herstellung eines Harn stoffderivates der Formel
EMI0001.0004
dadurch gekennzeichnet, dass man 3,4-Di- chloranilin seit Phosgen zu einem Derivat der 3,4-Dichlorphenylcarbaminsäure und die ses mit 2-Amino-4',5'-dichlor-1,1'-diphenyl- äther-4-sulfonsäure umsetzt.
Das neue Harn stoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Mottensehutzmittel.
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) '/2o Mol. der 2-Amino-4',5'-dichlor- 1,1'-diphenyläther-4-sulfonsäure wird in trockenem Pyridin gelöst und unter Rühren bei 1-15 C portionenweise mit 1j" 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 Rück stand 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 heissem 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 since phosgene to a derivative of 3,4-dichlorophenylcarbamic acid and this ses with 2-amino-4 ', 5'-dichloro-1,1'-diphenyl ether-4- sulfonic acid converts.
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.
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) '/ 2o mol. of the 2-amino-4', 5'-dichloro-1,1'-diphenylether-4-sulfonic acid is dissolved in dry pyridine and stirred in portions at 1-15 ° C. with 1j "mol. 3 , 4-dichlorophenyl isocyanate is added, and stirring is 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 obtained after separation, drying and grinding as a pale powder which is soluble in hot water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH212408T | 1938-06-16 | ||
| CH215314T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215314A true CH215314A (en) | 1941-06-15 |
Family
ID=25725194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215314D CH215314A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215314A (en) |
-
1938
- 1938-06-16 CH CH215314D patent/CH215314A/en unknown
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