CH215320A - Process for the production of a urea derivative. - Google Patents
Process for the production of a urea derivative.Info
- Publication number
- CH215320A CH215320A CH215320DA CH215320A CH 215320 A CH215320 A CH 215320A CH 215320D A CH215320D A CH 215320DA CH 215320 A CH215320 A CH 215320A
- Authority
- CH
- Switzerland
- Prior art keywords
- urea derivative
- production
- derivative
- hot water
- phosgene
- 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
- 239000000843 powder Substances 0.000 claims description 3
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 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
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 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
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 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
- 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
- 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
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-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 stoffderivates der Formel
EMI0001.0003
dadurch gekennzeichnet, dass man 3,4-Di- chloranilin mit Phosgen zu einem Derivat der 3,4-Dichlorphenyl:carbaminsäure und dieses mit 2-Amino-4-chlor-4'-tert.amyl-1,1'-diphe- nyläther-2'-sulfonsäure umsetzt.
Das neue Harnstoffderivat bildet als Natriumsalz ein helles, in heissem Wasser lösliches Pulver und eignet sich als Mottenschutzmittel. <I>Beispiel:</I> a) In 500 Teile Essigester, welche<B>13,5</B> Teile Phosgen enthalten, wird eine Lösung von 162 Teilen 3,4-Dichlaranilin in 1000 Tei- len Essigester langsam eingetropft, unter gleichzeitigem Durchleiten eines Phosgen- stromes. Nach Beendigung der Reaktion wird das Lösungsmittel in,
der Wärme abdestilliert, wobei das gebildete 3,4-Dichlorphenylcarb- aminsäurechlorid unter Salzsäureabspaltung in das 3,4-Dichlorphenylisocyanat übergeht.
b) '-/2o Mol. der 2-Amino-4-ehlor-4'-tert. amyl-1,1'-diphenyläther-2'-sulfonsäure wird in trockenem Pyridin .gelöst und unter Rüh ren bei 10 bis<B>15'</B> C portionenweise mit oho Mol. 3,4-Diehlorphenylisocyanat versetzt. Dann wird bei Raumtemperatur weiterge- rührt, bis keine freie Aminogruppe mehr nachweisbar ist.
Hierauf versetzt man mit Sodalösung bis zur alkalischen Reaktion und bläst das Pyridin mit Wasserdampf ab. Den Rückstand löst man in heissem Wasser, fil triert 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 viel hei ssem 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
EMI0001.0003
characterized in that 3,4-dichloroaniline with phosgene to a derivative of 3,4-dichlorophenyl: carbamic acid and this with 2-amino-4-chloro-4'-tert.amyl-1,1'-diphe- Nylether-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 162 parts of 3,4-dichlaraniline in 1000 parts of ethyl acetate is slowly added dropwise to 500 parts of ethyl acetate, which contain <B> 13.5 </B> parts of phosgene , with simultaneous passage of a phosgene stream. After the reaction has ended, the solvent is
distilled off the heat, the 3,4-dichlorophenylcarbamic acid chloride formed converting into the 3,4-dichlorophenyl isocyanate with elimination of hydrochloric acid.
b) '- / 2o mol. of 2-amino-4-chloro-4'-tert. amyl-1,1'-diphenyl ether-2'-sulfonic acid is dissolved in dry pyridine and an ohmic mole of 3,4-diehlophenyl isocyanate is added in portions at 10 to 15 ° C. while stirring. 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, the solution filtered, the reaction product precipitates as a gray resin by adding sodium chloride and, after separation, drying and grinding, it is obtained as a pale powder that is soluble in plenty of hot water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215320T | 1938-06-16 | ||
| CH212408T | 1938-06-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH215320A true CH215320A (en) | 1941-06-15 |
Family
ID=25725200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215320D CH215320A (en) | 1938-06-16 | 1938-06-16 | Process for the production of a urea derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH215320A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0765305A4 (en) * | 1994-06-02 | 1997-09-03 | Smithkline Beecham Corp | ANTI-INFLAMMATORY COMPOUNDS |
-
1938
- 1938-06-16 CH CH215320D patent/CH215320A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0765305A4 (en) * | 1994-06-02 | 1997-09-03 | Smithkline Beecham Corp | ANTI-INFLAMMATORY COMPOUNDS |
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