CH215312A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215312A CH215312A CH215312DA CH215312A CH 215312 A CH215312 A CH 215312A CH 215312D A CH215312D A CH 215312DA CH 215312 A CH215312 A CH 215312A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea derivative
- production
- reacted
- derivative
- acid
- 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
- NAQNRFQILKDCBK-UHFFFAOYSA-N 5-amino-2-(4-chloroanilino)benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1NC1=CC=C(Cl)C=C1 NAQNRFQILKDCBK-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
- 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
- 238000003756 stirring Methods 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
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-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
- BSWHYOQBJHPZJM-UHFFFAOYSA-N n-(3,4-dichlorophenyl)carbamoyl chloride Chemical compound ClC(=O)NC1=CC=C(Cl)C(Cl)=C1 BSWHYOQBJHPZJM-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 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
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 Harnstoifderivates. 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 die ses mit 4 - Amino -4'- chlordiphenylamin- 2 - sulfonsäure umsetzt.
Das neue Harnstoff derivat bildet als Natriumsalz ein helles, in Wasser schwerlösliches 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 geht.
b) '/2o Mol. der 4-Amino-4'-chlordiphenyl- amin-2-sulfonsäure wird in trockenen Py- ridin gelöst und unter Rühren bei 10-15 C portionenweise mit '/2o Mol. 3,4 - Dichlor- phenylisocyanat 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 Rüekstand 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 Mah- len als helles, in Wasser schwerlösliches Pulver.
Process for the production of a urea derivative. The present patent relates to 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 4-amino -4'-chlorodiphenylamine-2-sulfonic acid.
As a sodium salt, the new urea derivative forms a light-colored powder that is sparingly soluble in 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, the 3,4-dichlorophenylcarbamic acid chloride formed converting into the 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.
b) 1/2 mol. of the 4-amino-4'-chlorodiphenylamine-2-sulfonic acid is dissolved in dry pyridine and mixed in portions with 1/2 mol. 3,4-dichloro with stirring at 10-15 ° C. phenyl isocyanate added. 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. You solve the residue. in hot water, the solution is filtered, the reaction product precipitates as a gray resin by adding sodium chloride and, after separation, drying and grinding, receives it as a pale powder that is sparingly soluble in water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215312T | 1938-06-16 | ||
| CH212408T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215312A true CH215312A (en) | 1941-06-15 |
Family
ID=25725192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215312D CH215312A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215312A (en) |
-
1938
- 1938-06-16 CH CH215312D patent/CH215312A/en unknown
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