CH306855A - Process for the production of a condensation product. - Google Patents
Process for the production of a condensation product.Info
- Publication number
- CH306855A CH306855A CH306855DA CH306855A CH 306855 A CH306855 A CH 306855A CH 306855D A CH306855D A CH 306855DA CH 306855 A CH306855 A CH 306855A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- reacted
- amino
- sodium
- trifluoromethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000007859 condensation product Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims description 11
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- -1 sodium 2-amino-4-trifluoromethyl-benzenesulphonic acid Chemical compound 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 4
- RDEHTOWFTPLGID-UHFFFAOYSA-M [Na+].NC1=C(C=CC(=C1)C(F)(F)F)S(=O)(=O)[O-] Chemical compound [Na+].NC1=C(C=CC(=C1)C(F)(F)F)S(=O)(=O)[O-] RDEHTOWFTPLGID-UHFFFAOYSA-M 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 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 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- C07C309/45—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)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines Kondensationsproduktes.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Konden sationsproduktes der Formel
EMI1.1
dadurch gekennzeichnet, dass man 3-Chloranilin mit einem Halogenkohlensäurederivat reagieren lässt und das erhaltene reaktive Carbaminsäurederivat mit 2-amino-4-trifluormethyl-benzolsulfonsaurem Natrium umsetzt.
Eine Ausführungsform des erfindungsge- mässen Verfahrens besteht darin, dass man 3-Chlor-anilin mit Phosgen reagieren lässt und das erhaltene 3-Chlor-phenyl-l-carbamin- säurechlorid mit 2-amino-4-trifluormethyl- benzolsulfonsaurem Natrium umsetzt. Dabei arbeitet man vorzugsweise in Gegenwart einer tertiären Base als Kondensationsmittel, Pyridin oder Chinolin sind für diesen Zweek vor allem geeignet.
Des weiteren kann man 3-Chlor-anilin und Phosgen bei erhöhter Temperatur reagieren lassen und das erhaltene 3-Chlor-phenyl-1-isocyanat mit 2-amino-4-trifluormethyl-benzolsulfonsaurem Natrium zur Reaktion bringen, wobei man die Verbindung der obigen Formel in guter Ausbeute und vorzüglicher Reinheit erhält. Als Losungsmittel eignet sich für diese Art der Umsetzung vor allem Acetonitril oder Pyridin.
Schliesslich besteht eine Ausführungsform darin, dass man 3-Chlor-anilin mit einem Ha logenkohlensäureester reagieren lässt und den erhaltenen 3-Chlor-phenyl-1-carbaminsäure- ester mit 2-amino-4-trifluormethyl-benzolsul- fonsaurem Natrium umsetzt.
Als Halogenkohlensäureester kommen hauptschlich niedere Alkyl-oder Arylester in Frage. Der Umsatz kann vorteil. haft in Wasser vorgenommen werden.
Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar lösliches Kristallpulver, das als Mottenschutzmittel verwendet werden kann.
Beispiel 1 : a) 100 Teile trockenes Benzol werden bei 70 mit Phosgen gesättigt ; dazu wird unter Riihren und Einleiten von Phosgen eine Losung von 33 Teilen 3-Chlor-anilin in 100 Teilen trockenem Benzol bei 65-70 zugetropft.
Nach einiger Zeit erhitzt man bis zum Rüekfluss und leitet so lange Phosgen ein, bis nur noch kleine Mengen des verwendeten Amins ungelöst sind. Die benzolische Lösung wird hierauf filtriert, das Benzol abdestilliert und das 3-Chlor-phenyl-1-isocyanat fraktioniert.
Kp21 94 , Ausbeute 31 Teile. b) 13, 15 Teile 2-amino-4-trifluormethyl- benzolsulfonsaures Natrium werden in 180 Teilen trockenem Acetonitril gelöst, mit 7, 7 Teilen 3-Chlor-phenyl-1-isocyanat versetzt und fünf Stunden auf dem Wasserbad erwärmt.
Die Reaktionslösung wird filtriert und das Lösungsmittel verda. mpft. Ausbeute 15, 5 Teile.
Das neue Kondensationsprodukt bildet naeh dem Trocknen und Mahlen ein helles, in heissem Wasser klar losliches Pulver.
Beispiel 2 :
Das aus Phosgen und 3-Chlor-anilin in einem trockenen inerten Losungsmittel liergestellte 3-Chlor-phenyl-1-earbaminsäureehlorid ergibt unter Zusatz von Pyridin als Kondensationsmittel mit 2-amino-4-trifluormethyl- benzolsulfonsaurem Natrium den in Beispiel l b) besehriebenen Harnstoff in befriedigender Ausbeute.
Beispiel 3 :
Der aus Chlorkohlensäurephenylester und 3-Chlor-anilin in trockenem Pyridin hergestellte 3-Chlor-plienyl-1-carbaminsäurephenyl- ester liefert dureh LTmsetzung mit 2-amino-4trifluormethyl-benzolsulfonsaurem Natrium in heissem Wasser den in Beispiel 1 b) beschriebenen Harnstoff. Anstatt des 3-Chlor- phenyl-1-carbaminsäurephenylesters kann auch der entsprechende Methylester verwen- det werden.
Process for the production of a condensation product.
The present patent relates to a process for the preparation of a condensation product of the formula
EMI1.1
characterized in that 3-chloroaniline is allowed to react with a halocarbonic acid derivative and the reactive carbamic acid derivative obtained is reacted with sodium 2-amino-4-trifluoromethyl-benzenesulphonic acid.
One embodiment of the process according to the invention is that 3-chloro-aniline is allowed to react with phosgene and the 3-chloro-phenyl-1-carbamic acid chloride obtained is reacted with sodium 2-amino-4-trifluoromethylbenzenesulphonic acid. It is preferred to work in the presence of a tertiary base as the condensing agent; pyridine or quinoline are especially suitable for this purpose.
In addition, 3-chloro-aniline and phosgene can be allowed to react at elevated temperature and the 3-chloro-phenyl-1-isocyanate obtained can be reacted with sodium 2-amino-4-trifluoromethyl-benzenesulfonate, the compound of the above formula obtained in good yield and excellent purity. Acetonitrile or pyridine are particularly suitable as solvents for this type of reaction.
Finally, in one embodiment, 3-chloro-aniline is allowed to react with a halogenated carbonate and the 3-chloro-phenyl-1-carbamic acid ester obtained is reacted with sodium 2-amino-4-trifluoromethyl-benzenesulfonate.
Mainly lower alkyl or aryl esters are suitable as halocarbonic acid esters. Sales can be beneficial. can be made in water.
The new condensation product forms a pale crystal powder that is clearly soluble in hot water and can be used as a moth repellent.
Example 1: a) 100 parts of dry benzene are saturated at 70 with phosgene; To this end, a solution of 33 parts of 3-chloro-aniline in 100 parts of dry benzene at 65-70 is added dropwise while stirring and passing in phosgene.
After some time, the mixture is heated until it is refluxed and phosgene is introduced until only small amounts of the amine used are undissolved. The benzene solution is then filtered, the benzene is distilled off and the 3-chloro-phenyl-1-isocyanate is fractionated.
Bp21 94, yield 31 parts. b) 13.15 parts of sodium 2-amino-4-trifluoromethylbenzenesulphonic acid are dissolved in 180 parts of dry acetonitrile, 7.7 parts of 3-chlorophenyl-1-isocyanate are added and the mixture is heated on a water bath for five hours.
The reaction solution is filtered and the solvent is diluted. fumes. Yield 15.5 parts.
After drying and grinding, the new condensation product forms a light-colored powder that dissolves clearly in hot water.
Example 2:
The 3-chloro-phenyl-1-earbamic acid chloride prepared from phosgene and 3-chloro-aniline in a dry, inert solvent gives, with addition of pyridine as a condensing agent with sodium 2-amino-4-trifluoromethylbenzenesulfonic acid, the urea described in Example 1b) satisfactory yield.
Example 3:
The 3-chloroplienyl-1-carbamic acid phenyl ester prepared from chlorocarbonic acid phenyl ester and 3-chloro-aniline in dry pyridine gives the urea described in Example 1 b) by reacting with sodium 2-amino-4-trifluoromethyl-benzenesulfonic acid in hot water. Instead of the 3-chlorophenyl-1-carbamic acid phenyl ester, the corresponding methyl ester can also be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH306855T | 1950-12-26 | ||
| CH300283T | 1950-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306855A true CH306855A (en) | 1955-04-30 |
Family
ID=25734244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306855D CH306855A (en) | 1950-12-26 | 1950-12-26 | Process for the production of a condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306855A (en) |
-
1950
- 1950-12-26 CH CH306855D patent/CH306855A/en unknown
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