CH215327A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215327A CH215327A CH215327DA CH215327A CH 215327 A CH215327 A CH 215327A CH 215327D A CH215327D A CH 215327DA CH 215327 A CH215327 A CH 215327A
- Authority
- CH
- Switzerland
- Prior art keywords
- dichloro
- urea derivative
- production
- derivative
- phosgene
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process 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
- 239000004552 water soluble 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- -1 3,5-dichloro-2-phenetidine Chemical compound 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
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 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
- 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
- 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
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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 Harnstoüderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Harn stoffderivates der Formel
EMI0001.0003
dadurch gekennzeichnet, dass man 3,5-Di- chlor-2-phenetidin mit Phosgen zu einem Derivat der 3,5-Dichlor-2-äthogyphenylcarb- aminsäure und dieses mit 2-Amin.o-4,4'-di-! chlor-1,1'-diphenyläther-2'-sulfonsäure um setzt.
Das neue Harnstoffderivat bildet als Natriumsalz ein helles, in Wasser lösliches Pulver und eignet sich als Mottenschutz mittel.
Beispiel: a) In 500 Teile Essigester, welche 135 Teile Phosgen enthalten, wirdeineLösung von 207 Teilen 3,5-Dichlor-2-phenetidin in<B>1000</B> Teilen Essigester langsam eingetropft unter gleichzeitigem Durchleiten eines Phosgen- strames. Nach Beendigung der Reaktion wird das Lösungsmittel in der Wärme ab destilliert, wobei das gebildete 3,
5-Dichlor- 2-äthogy-phenylcarbaminsäurechlflrid unter Salzsäureabspaltung in das 3,5-Dichlor-2- äthogyphenylisocyanat vom $p." 145 über geht.
b) 'J") Mol. der 2-Amino-4,4'-dichlor-1,1'- diphenyläther-2'-@sulfonsäure wird in trocke nem Pyridin gelöst und unter Rühren bei 10-15 C portionenweise mit '/2o Mol. 3,5- Dichlor- 2 - äthogyphenylisocyanat versetzt. Dann wird bei Raumtemperatur weiterge rührt, bis keine freie Aminogruppe mehr nachweisbar ist.
Hierauf versetzt man mit Sololösung bis zur alkalischen Reaktion und bläst das Pyridin mit Wasserdampf ab. Den Rückstand löst man in heissem Wasser, filtriert die Lösung, fällt das Reaktions- produkt durch Zugabe von Kochsalz als graues Harz aus und erhält es nach dem Ah- trennen, Trocknen und Mahlen als helles, in Wasser lösliches Pulver.
Process for the production of a urinary derivative. The subject of the present patent is a process for the preparation of a urea derivative of the formula
EMI0001.0003
characterized in that 3,5-dichloro-2-phenetidine with phosgene to a derivative of 3,5-dichloro-2-äthogyphenylcarb- aminsäure and this with 2-Amin.o-4,4'-di-! chlorine-1,1'-diphenylether-2'-sulfonic acid sets.
The new urea derivative forms a pale, water-soluble powder as a sodium salt and is suitable as a moth repellent.
Example: a) A solution of 207 parts of 3,5-dichloro-2-phenetidine in 1000 parts of ethyl acetate is slowly added dropwise to 500 parts of ethyl acetate containing 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, whereby the 3 formed
5-dichloro-2-ethogyphenylcarbamic acid chloride is converted into 3,5-dichloro-2-ethogyphenyl isocyanate from $ 145 with elimination of hydrochloric acid.
b) 'J ") Mol. The 2-amino-4,4'-dichloro-1,1'-diphenylether-2' - @ sulfonic acid is dissolved in dry pyridine and stirred in portions at 10-15 C with '/ 20 moles of 3,5-dichloro-2-ethogyphenyl isocyanate are added, and stirring is continued at room temperature until free amino groups can no longer be detected.
Solo solution is then added until an alkaline reaction is achieved and the pyridine is blown off with steam. The residue is dissolved in hot water, the solution is filtered, the reaction product precipitates as a gray resin by adding sodium chloride and, after separating, drying and grinding, it is obtained as a pale, water-soluble powder.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215327T | 1938-06-16 | ||
| CH212408T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215327A true CH215327A (en) | 1941-06-15 |
Family
ID=25725207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215327D CH215327A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215327A (en) |
-
1938
- 1938-06-16 CH CH215327D patent/CH215327A/en unknown
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