CH215329A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215329A CH215329A CH215329DA CH215329A CH 215329 A CH215329 A CH 215329A CH 215329D A CH215329D A CH 215329DA CH 215329 A CH215329 A CH 215329A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea derivative
- production
- derivative
- acid
- trichlorophenylcarbamic
- 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
- GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-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
- GNHDFMREUIJRPV-UHFFFAOYSA-N n-(2,4,5-trichlorophenyl)carbamoyl chloride Chemical compound ClC(=O)NC1=CC(Cl)=C(Cl)C=C1Cl GNHDFMREUIJRPV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- KVEROPFXBPXHCI-UHFFFAOYSA-N (2,4,5-trichlorophenyl)carbamic acid Chemical class OC(=O)NC1=CC(Cl)=C(Cl)C=C1Cl KVEROPFXBPXHCI-UHFFFAOYSA-N 0.000 description 1
- RDUIJJYNVCVETK-UHFFFAOYSA-N 1,2,4-trichloro-5-isocyanatobenzene Chemical compound ClC1=CC(Cl)=C(N=C=O)C=C1Cl RDUIJJYNVCVETK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 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
- C07C309/41—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 Harnstoffderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Harn- stoffderivates der Formel
EMI0001.0007
dadurch gekennzeichnet, dass man 2,4,5-Tri- chloranilin mit Phosgen zu einem Derivat der 2,4,5-Trichlorphenylcarbaminsäure und dieses mit 2-Amino-4,4'-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.
<I>Beispiel:</I> a) In 500 Teile Essigester, welche 135 Teile Phosgen enthalten, wird eine Lösung von 196 Teilen 2,4,5-Trichloranilin in 1000 Teilen Essigester langsam eingetropft unter gleichzeitigem Durchleiten eines. Phosgen- stromes.. Nach Beendigung der Reaktion wird das Lösungsmittel in der Wärme abd@estil- liert, wobei das gebildete 2,4,5-Trichlor- phenylcarbaminsäurechlorid unter Salzsäure abspaltung in das 2,4,
5-Trichlorphenyliso- cyanat übergeht.
b) '/2o Mol. der 2-Amino-4,4'-dichlor-1,1'- diphenyläth-er-2'-.sulfonsäure wird in trocke nem Pyridin gelöst und unter Rühren bei l0-15 C portionenweise mit1/zo Mol. 2,4,5- Trichlorphenylisocyanat versetzt. Dann wird bei Raumtemperatur weitergerührt, bis keine freie Aminogruppe mehr nachweisbar ist.
hierauf versetzt man mit Soda-lösung bis zur alkalischen Reaktion und bläst das Pyridin mit Wasserdampf ab. Den Rückstand löst man in heissem Wasser, filtriert die Lösung, fällt das Reaktionsprodukt durch Zugabe von Kochsalz als graues Harz aus und er- hält es nach dem Abtrennen, Trocknen und Mahlen als helles, in heissem Wasser lösliches 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
EMI0001.0007
characterized in that 2,4,5-trichloroaniline with phosgene to a derivative of 2,4,5-trichlorophenylcarbamic acid and this with 2-amino-4,4'-dichloro-1,1'-diphenyl ether- 2 ' -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.
<I> Example: </I> a) A solution of 196 parts of 2,4,5-trichloroaniline in 1000 parts of ethyl acetate is slowly added dropwise to 500 parts of ethyl acetate which contain 135 parts of phosgene, while a solution is simultaneously passed through. Phosgene stream .. After the reaction has ended, the solvent is removed in the heat, the 2,4,5-trichlorophenylcarbamic acid chloride formed being split off into the 2,4,5-trichlorophenylcarbamic acid chloride with hydrochloric acid
5-trichlorophenyl isocyanate passes over.
b) '/ 2o mol. of 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 1 / zo mol. 2,4,5-trichlorophenyl isocyanate added. Stirring is then continued at room temperature until free amino groups can no longer be detected.
Soda solution is then added to an alkaline reaction 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 the addition of 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 |
|---|---|---|---|
| CH215329T | 1938-06-16 | ||
| CH212408T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215329A true CH215329A (en) | 1941-06-15 |
Family
ID=25725209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215329D CH215329A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215329A (en) |
-
1938
- 1938-06-16 CH CH215329D patent/CH215329A/en unknown
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