CH215309A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215309A CH215309A CH215309DA CH215309A CH 215309 A CH215309 A CH 215309A CH 215309D A CH215309D A CH 215309DA CH 215309 A CH215309 A CH 215309A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea derivative
- methyl
- production
- amino
- methoxy
- 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
- KXEKUVPQDXOCBG-UHFFFAOYSA-N 5-chloro-2-methoxy-4-methylaniline Chemical compound COC1=CC(C)=C(Cl)C=C1N KXEKUVPQDXOCBG-UHFFFAOYSA-N 0.000 claims description 3
- 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
- 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
- -1 derivative of 2-methoxy-4-methyl-5-chlorophenylcarbamic acid Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- POHWYAUWTLPFFV-UHFFFAOYSA-N 1-chloro-5-isocyanato-4-methoxy-2-methylbenzene Chemical compound COC1=CC(C)=C(Cl)C=C1N=C=O POHWYAUWTLPFFV-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
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 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
- 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 Harnstoffderivates. Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Harn stoff derivates der Formel
EMI0001.0003
dadurch gekennzeichnet, dass man 1-Amino- 2-methoxy-4-methyl-5-chlorbenzol mit Phos- gen zu einem Derivat der 2 - Methoxy - 4- methyl-5-chlorphenylcarbaminsäure und die ses mit 2-Amino-4,4'-dichlor-1,1'-diphenyl- äther-2'-sulfonsäure umsetzt.
Das neue Harn stoffderivat bildet als Natriumsalz ein helles, in 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 169 Teilen 1-Amino-2-methoxy-4-methyl- 5-chlorbenzol in 1000 Teilen Essigester lang sam eingetropft unter gleichzeitigem Durch leiten eines Phosgenstromes. Nach Beendi gung der Reaktion wird das Lösungsmittel in der Wärme abdestilliert, wobei das ,
ge bildete 2-Methoxy-4-methyl-5-chlorphenyl- carbaminsäurechlorid unter Salzsäureabspal- tung in das 2-Methoxy-4-methyl-5-chlor- phenylisocyanat vom gp." 145-148 über geht.
b) 1/_o Mol. der 2-Amino-4,4'-dichlor-1,1'- diphenyläther-2'-sulfonsäure wird in trocke nem Pyridin gelöst und unter Rühren bei <B>10-15'</B> C portionenweise mit '/2p Mol. 2- Methoxy-4- methyl - 5 - clilorphenylisocy anat versetzt.
Dann -#vird 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 Reaktionspro- dukt durch Zugabe von Kochsalz als graues Harz aus und erhält es nach dem Abtrennen, Trocknen und Mahlen als helles, in Wasser lösliches Pulver.
Process for the production of a urea derivative. The present patent is a process for the preparation of a urea derivative of the formula
EMI0001.0003
characterized in that 1-amino-2-methoxy-4-methyl-5-chlorobenzene is used with phosgene to form a derivative of 2-methoxy-4-methyl-5-chlorophenylcarbamic acid and this with 2-amino-4,4 '-dichloro-1,1'-diphenyl ether-2'-sulfonic acid is converted.
The new urea derivative forms a pale, water-soluble powder as a sodium salt and is suitable as a moth repellent.
<I> Example: </I> a) In. 500 parts of ethyl acetate containing 135 parts of phosgene, a solution of 169 parts of 1-amino-2-methoxy-4-methyl-5-chlorobenzene in 1000 parts of ethyl acetate is slowly added dropwise with simultaneous passage of a phosgene stream. After the end of the reaction, the solvent is distilled off in the heat, the
The 2-methoxy-4-methyl-5-chlorophenylcarbamic acid chloride formed is converted into the 2-methoxy-4-methyl-5-chlorophenyl isocyanate of gp. "145-148 with elimination of hydrochloric acid.
b) 1 / _o mol. of 2-Amino-4,4'-dichloro-1,1'-diphenylether-2'-sulfonic acid is dissolved in dry pyridine and stirred at 10-15 '/ B > C in portions with 1/2 p mol. 2-methoxy-4-methyl-5-clilorphenyl isocyanate added.
The 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. If 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 |
|---|---|---|---|
| CH215309T | 1938-06-16 | ||
| CH212408T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215309A true CH215309A (en) | 1941-06-15 |
Family
ID=25725189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215309D CH215309A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215309A (en) |
-
1938
- 1938-06-16 CH CH215309D patent/CH215309A/en unknown
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