CH306845A - Process for the production of a condensation product. - Google Patents
Process for the production of a condensation product.Info
- Publication number
- CH306845A CH306845A CH306845DA CH306845A CH 306845 A CH306845 A CH 306845A CH 306845D A CH306845D A CH 306845DA CH 306845 A CH306845 A CH 306845A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- trifluoromethyl
- aniline
- reacted
- amino
- 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 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- -1 2-amino-3 -chlor-6-trifluoromethyl-benzenesulfonic acid sodium Chemical compound 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- WHCTXSLMHTZUAC-UHFFFAOYSA-N 2-amino-3-chloro-6-(trifluoromethyl)benzenesulfonic acid Chemical compound ClC1=C(N)C(=C(C=C1)C(F)(F)F)S(=O)(=O)O WHCTXSLMHTZUAC-UHFFFAOYSA-N 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- WGNNILPYHCKCFF-UHFFFAOYSA-N 2-chloro-n-methylaniline Chemical compound CNC1=CC=CC=C1Cl WGNNILPYHCKCFF-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 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
- 238000006243 chemical reaction Methods 0.000 description 4
- 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
- YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 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
- 238000010992 reflux Methods 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 Herstellu7ng eines Konden- sationsproduktes der Formel
EMI1.1
dadurch gekennzeichnet, dass man 3-Trifluor- methyl-6-chlor-anilin mit einem Halogenkoh lensäurederivat reagieren lässt und das erhal- tene reaktive Carbaminsäurederivat mit 2- amino-3-chlor-6-trifluormethyl-benzolsulfonsaurem Natrium umsetzt.
Eine Ausführlmgsform des erfindungsge massen Verfahrens besteht darin, dass man 3-Triiluormethyl-6-ehlor-anilin mit Phosgen reagieren lässt und das erhaltene 3-Trifluor metllyl-6-elllor-pheny]-1-earbaminsäuree, hlorid mit 2-amino-3-chlor-6-trifluormethyl-benzolsul i'onsaurem Natrium umsetzt. Dabei arbeitet man vorzugsweise in Gegenwart einer tertiä- ren Base als Kondensationsmittel Pyridin oder Chinolin sind für diesen Zweck vor allem geeigllet.
Des weiteren kann man 3-Trifluormethyl6-chlor-anilin und Phosgen bei erhöhter Temperatur reagieren lassen und das erhaltene 3-Trifluormethyl-6-chlor-phenyl-1-isocyanat mit 2 amino-3-chlor-6-trifluormethyl-benzol- snlfonsaurem Natrium zur Realçtion 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-Trifluormethyl-6-chlor-anilin mit einem Halogenkohlensäureester reagieren lässt und den erhaltenen 3-Trifluormethyl- 6-chlor-phenyl-1-carbaminsäureester mit 2 amino-3-chlor-6-trifluormethyl-benzolsulfon- saurem Natrium umsetzt.
Als Halogenkohlensäureester kommen hauptschlich niedere Alkyl-oder Arylester in Frage. Der Umsatz kann vorteilhaft in Wasser vorgenommen werden.
Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar lösliehes Kri stallpulver, das als Mottenschutzmittel verwendet werden kann.
Betspt6 1 : a) 300 Teile trockenes Benzol werden bei 70 mit Phosgen gesättigt ; dazu wird tinter Rührcn und Einleiten von Phosgen eine Lösung von 100 Teilen 3-Trifluormethyl-6-chor- anilin in 300 Teilen trockenem Benzol bei 65 bis 70 zugetropft. NTach einiger Zeit erhitzt man bis zum Rückfluss und leitet so lange Phosgen ein, bis nur noch kleine Mengen des verwendeten Amins ungelöst sind. Die benzo- Hsehe Losung wird hierauf filtriert, das Benzol abdestilliert und das 3-Trifluormethyl-6- chlor-phenyl-1-isocyanat fraktioniert.
Kp 122-124" ; Ausbeute 90 Teile. b) 9, 9 Teile 2-amino-3-chlor-6-trifluor- metjhyl-benzolsulfonsaures Natrium werden in 140 Teilen trockenem Acetonitril gelöst, mit 7, 4 Teilen 3-Trifluormethyl-6-chlor-phenyl-l- isoeyanat versetzt und sechs Stunden auf dem Wasserbad erwärmt. Die Reaktionslosung wird filtriert md das Lösungsmittel verdampft. Ausbeute 10, 5 Teile.
Das neue Kondensationsprodnlkt bildet nach dem Trocknen und Mahlen ein helles, in heissem Wasser klar lösliches Pulver.
Beispie. 1 9, :
Das aus Phosgen und 3-Trifluormethy]-6- chlor-anilin in einem trockenen inerten Lösungsmittel hergestellte 3-Trifluormethyl-6 chlor-phenyl-1-carbaminsäurechlorid ergibt unter Zusatz von Pyridin als Kondensations- mittel mit 2-amino-3-ehlor-6-trifluormethyl- benzolsulfonsaurem Natrium den in Beispiel 1 b) beschriebenen Harnstoff in befriedigender Ausbeute.
Beispiel 3 :
Der aus Chlorkohlensäurephenylester und 3-Trifluormethyl-6-chlor-anilin in trockenem Pyridin hergestellte 3-Trifluormethyl-6-chlor- phenyl-1-carbaminsäurephenylester liefert dureli Umsetzung mit 2-amino-3-chlor-6-tri- fluormethyl-benzolsulfonsauremNatrium in heissem Wasser den in Beispiel 1 b) beschriebenen Harnstoff. Anstatt des 3-Trifluor- methyl-6-chlor-phenyl-1-carbaminsäurephenyl- esters kann auch der entsprechende Methylester verwendet werden.
Process for the production of a condensation product.
The subject of the present patent is a process for the production of a condensation product of the formula
EMI1.1
characterized in that 3-trifluoromethyl-6-chloro-aniline is allowed to react with a halogenated carbonic acid derivative and the reactive carbamic acid derivative obtained is reacted with sodium 2-amino-3-chloro-6-trifluoromethyl-benzenesulfonic acid.
One embodiment of the process according to the invention consists in allowing 3-triiluomethyl-6-chloroaniline to react with phosgene and the 3-trifluoromethyl-6-ellloropheny] -1-earbamic acid obtained, chloride with 2-amino-3 -chlor-6-trifluoromethylbenzenesul i'onsaurem sodium converts. It is preferable to work in the presence of a tertiary base as the condensing agent. Pyridine or quinoline are especially suitable for this purpose.
Furthermore, 3-trifluoromethyl-6-chloro-aniline and phosgene can be allowed to react at elevated temperature and the 3-trifluoromethyl-6-chloro-phenyl-1-isocyanate obtained with sodium 2-amino-3-chloro-6-trifluoromethyl-benzene-sulfonic acid bring to realization, the compound of the above formula being obtained in good yield and excellent purity. A particularly suitable solvent for this type of reaction is acetonitrile. or pyridine.
Finally, one embodiment consists in allowing 3-trifluoromethyl-6-chloro-aniline to react with a halocarbon acid ester and the 3-trifluoromethyl-6-chloro-phenyl-1-carbamic acid ester obtained with 2-amino-3-chloro-6-trifluoromethyl- benzenesulphonic acid sodium.
Mainly lower alkyl or aryl esters are suitable as halocarbonic acid esters. The conversion can advantageously be carried out in water.
The new condensation product forms a pale crystal powder that dissolves clearly in hot water and can be used as a moth repellent.
Betspt6 1: a) 300 parts of dry benzene are saturated with phosgene at 70; to this end, a solution of 100 parts of 3-trifluoromethyl-6-chloroaniline in 300 parts of dry benzene at 65 to 70 is added dropwise while stirring and passing in phosgene. After a while, the mixture is heated to reflux and phosgene is introduced until only small amounts of the amine used are undissolved. The benzo-Hsehe solution is then filtered, the benzene is distilled off and the 3-trifluoromethyl-6-chloro-phenyl-1-isocyanate is fractionated.
Bp 122-124 "; Yield 90 parts. B) 9.9 parts of 2-amino-3-chloro-6-trifluoromethyl-benzenesulphonic acid are dissolved in 140 parts of dry acetonitrile, with 7.4 parts of 3-trifluoromethyl-6 -chlorophenyl-l-isoeyanate is added and the mixture is heated on the water bath for six hours. The reaction solution is filtered and the solvent is evaporated. Yield 10.5 parts.
After drying and grinding, the new condensation product forms a pale powder that is clearly soluble in hot water.
Example 1 9,:
The 3-trifluoromethyl-6-chlorophenyl-1-carbamic acid chloride prepared from phosgene and 3-trifluoromethyl] -6-chloro-aniline in a dry, inert solvent gives, with the addition of pyridine as a condensing agent with 2-amino-3-chloro- Sodium 6-trifluoromethylbenzenesulfonic acid the urea described in Example 1 b) in a satisfactory yield.
Example 3:
The 3-trifluoromethyl-6-chlorophenyl-1-carbamic acid phenyl ester prepared from chlorocarbonic acid phenyl ester and 3-trifluoromethyl-6-chloro-aniline in dry pyridine gives dureli reaction with 2-amino-3-chloro-6-trifluoromethyl-benzenesulfonic acid sodium in hot water the urea described in Example 1 b). Instead of the 3-trifluoromethyl-6-chloro-phenyl-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 |
|---|---|---|---|
| CH300283T | 1950-12-26 | ||
| CH306845T | 1950-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306845A true CH306845A (en) | 1955-04-30 |
Family
ID=25734234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306845D CH306845A (en) | 1950-12-26 | 1950-12-26 | Process for the production of a condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306845A (en) |
-
1950
- 1950-12-26 CH CH306845D patent/CH306845A/en unknown
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