CH304943A - Process for the production of a condensation product. - Google Patents
Process for the production of a condensation product.Info
- Publication number
- CH304943A CH304943A CH304943DA CH304943A CH 304943 A CH304943 A CH 304943A CH 304943D A CH304943D A CH 304943DA CH 304943 A CH304943 A CH 304943A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- trifluoromethyl
- amino
- react
- allowed
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000011734 sodium Substances 0.000 claims description 10
- 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 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- ASPDJZINBYYZRU-UHFFFAOYSA-N 5-amino-2-chlorobenzotrifluoride Chemical compound NC1=CC=C(Cl)C(C(F)(F)F)=C1 ASPDJZINBYYZRU-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WUFCWZBEGPHDEE-UHFFFAOYSA-N n-[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(F)(F)C1=CC(NC(Cl)=O)=CC=C1Cl WUFCWZBEGPHDEE-UHFFFAOYSA-N 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- NBJZEUQTGLSUOB-UHFFFAOYSA-N 1-chloro-4-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(N=C=O)=CC=C1Cl NBJZEUQTGLSUOB-UHFFFAOYSA-N 0.000 claims description 2
- CXQYJPUBFUDFGQ-UHFFFAOYSA-N [4-chloro-3-(trifluoromethyl)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 CXQYJPUBFUDFGQ-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
- -1 halocarbon ester Chemical class 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 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
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- RDNQDSKTTPSVKZ-UHFFFAOYSA-N phenyl n-[4-chloro-3-(trifluoromethyl)phenyl]carbamate Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)OC=2C=CC=CC=2)=C1 RDNQDSKTTPSVKZ-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride 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 Kondensationsproduktes.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Konden sationsprodnktes der Formel
EMI1.1
dadureh gekennzeichnet, dass man 4-Chlor-5- trifluormethyl-anilin mit einem Halogenkoh tcnsäurederivat. reagieren lässt und das erhaltene reaktive Carbaminsäurederivat mit 2amino-3', 4,4'-trichlor-1,1'-diphenylÏther-6'-sul fonsaurem Natrium umsetzt.
Eine Ausführungsform des erfindungsgemässen Verfahrens besteht darin, dass man 4-Chlor-5-trifluormethyl-anilin mit Phosgen reagieren lässt und das erhaltene 4-Chlor5 - trifluormethyl-phenyl-carbaminsÏurechlorid mit 2-amino-3', 4, 4'-trichlor-1, 1'-diphenylather- 6'-sulfonsaurem Na. trium umsetzt. Dabei a. rbeitet man vorzugsweise in Gegenwart einer ter tiären Base als Kondensationsmittel. Pyridin oder Chinolin sind für diesen Zweek vor allem geeignet.
Des weitern kann man 4-Chlor-5-trifluor- methyl-anilin mit Phosgen bei erhöhter Temperatur umsetzen und das erhaltene 4-Chlor 5-trifluormethyl-phenyl-isocyanat mit 2-amino3', 4, 4'-trichlor-1, 1'-diphenylather- 6'-sulfonsau- rem Natrium zur Reaktion bringen, wobei man die Verbindung der obigen Formel in guter Ausbeute und vorziiglicher Reinheit erhält. Als Losungsmittel eignet sich für diese Art der Umsetzung vor allem Acetonitril.
Schliesslich besteht eine Ausführungsform dari, n, da-ss man4-Chlor-5-trifluormethyl-a. nilin mit einem Halogenkohlensäureester reagieren lϯt und den erhaltenen 4-Chlor-5-trifluor- methyl-phenyl-carbaminsÏureester mit 2-amino3', 4, 4'-trichlor-1, 1'- diphenylather-6'-sulionsau- rem Natrum. umsetzt.
Als HalogenkohlensÏureester kommen haupt- sächlich niedere Alkyl-oder Arylester in Frage. Der Umsatz ka. nn vorteilhaft in Wasser vorgenommen werden.
Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar losliches Kristallpulver, das als Mottensehutzmittel verwendet werden kann.
Beispiel 1 : a) 300 Teile trockenes Benzol werden bei 700 mit Phosgen gesättigt : dazu wird unter Rühren und Einleiten von Phosgen eine Losung von 100 Teilen 4-Chlor-5-trifluormethyl- anilin in 300 Teilen trockenem Benzol bei 65 bis 70 zugetropft. Nach 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- lisehe Losung wird hierauf filtriert, das Ben- zol abdestilliert und das 4-Chlor-5-trifluormethyl-isocyanat fraktioniert.
K14 : 92¯ ; Ausbeute : 81"/o.. b) 13, 02 Teile 2-amino-3', 4, 4'-triehlor-l, l'- diphenyläther-6'-sulfonsaures Natrium werden in 60 Teilen Acetonitril gelöst, mit 7, 38 Teilen 4-Chlor-5-trifluormethyl-phenyl-isoeyanat versetzt und vier Stunden auf dem Wasserbad erwärmt. Die Reaktionslösung wird filtriert und das Lösungsmittel verdampft. Ausbeute : 17 Teile.
Das Kondensationsprodukt wird in 3000 Teilen Wasser von 80-85¯ gel¯st, mit wenig Tierkohle versetzt und heiss filtriert. Naeh Zugabe von 65 Teilen gesättigter Koehsalz- lösung scheidet sich das Kondensationsprodukt aus. Nach dem Erkalten wird es gesam- melt und im Vakuum getrocknet. Um es von Kochsalz zu befreien, kann es aus absolutem Alkohol ausgezogen werden. Das neue Kondensationsprodukt bildet naeli dem Trocknen und Mahlen ein helles, in heissem Wasser klar lösliehes Pulver.
Beispiel 2:
Das aus Phosgen und 4-CMor-5-trifluor- methyl-anilin in einem trockenen inerten Lösungsmittel hergestellte 4-Chlor-5-trifluormethyl-phenyl-carbaminsÏurechlorid ergibt unter Zusatz von Pyridin als Kondensationsmittel mit 2-amino-3', 4, 4'-triehlor-l, l'-diphenyläther- 6'-sulfonsaurem Natrium den in Beispiel lb) beschriebenen Harnstoff in befriedigender Ausbeute.
Beispiel 3 :
Der aus Chlorkohlensäurephenylester und 4-Chlor-5-trifluormethyl-anilin in troekenem Pvridin hergestellte 4-Chlor-5-trifluormethyl- phenyl-carbaminsäurephenylester liefert durch Umsetzung mit 2-amino-3', 4, 4'-triehlor-1, 1'-diphenyläther-6'-sulfonsaurem Natrium in hei ssem Wasser den in Beispiel 1 b) beschrie- benen Harnstoff ; anstatt des 4-Clllor-5-tri- fluormethyl-phenyl-carbaminsÏurephenylesters 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 preparation of a condensation product of the formula
EMI1.1
characterized by the fact that 4-chloro-5-trifluoromethyl-aniline is used with a halogenated alcohol derivative. lets react and the reactive carbamic acid derivative obtained is reacted with 2 amino-3 ', 4,4'-trichloro-1,1'-diphenylÏther-6'-sulphonic acid sodium.
One embodiment of the process according to the invention is that 4-chloro-5-trifluoromethyl-aniline is allowed to react with phosgene and the 4-chloro-5-trifluoromethyl-phenyl-carbamic acid chloride obtained is treated with 2-amino-3 ', 4, 4'-trichloro 1,1'-diphenyl ether-6'-sulfonic acid Na. trium implements. Thereby a. one works preferably in the presence of a tertiary base as a condensing agent. Pyridine or quinoline are particularly suitable for this purpose.
Furthermore, 4-chloro-5-trifluoromethyl-aniline can be reacted with phosgene at elevated temperature and the 4-chloro 5-trifluoromethyl-phenyl-isocyanate obtained with 2-amino3 ', 4, 4'-trichloro-1, 1 bring '-diphenylether-6'-sulfonic acid sodium to the reaction, whereby the compound of the above formula is obtained in good yield and excellent purity. A particularly suitable solvent for this type of reaction is acetonitrile.
Finally, one embodiment consists in that there is 4-chloro-5-trifluoromethyl-a. Niline reacts with a halocarbon ester and the 4-chloro-5-trifluoromethyl-phenyl-carbamic acid ester obtained reacts with 2-amino3 ', 4, 4'-trichloro-1, 1'-diphenyl ether-6'-sulionic acid Natrum. implements.
Lower alkyl or aryl esters are mainly suitable as halocarbons. Sales ka. nn can advantageously be carried out in water.
The new condensation product forms a light-colored crystal powder that dissolves clearly in hot water and can be used as a moth repellent.
Example 1: a) 300 parts of dry benzene are saturated with phosgene at 700: to this end, a solution of 100 parts of 4-chloro-5-trifluoromethylaniline in 300 parts of dry benzene at 65 to 70 is added dropwise with stirring and introduction of phosgene. After some time, the mixture is heated to reflux and phosgene is passed in until only small amounts of the amine used are undissolved. The benzene solution is then filtered, the benzene is distilled off and the 4-chloro-5-trifluoromethyl isocyanate is fractionated.
K14: 92¯; Yield: 81 "/ o .. b) 13.02 parts of 2-amino-3 ', 4, 4'-triehlor-l, l'-diphenyl ether-6'-sulfonic acid sodium are dissolved in 60 parts of acetonitrile, with 7, 38 parts of 4-chloro-5-trifluoromethyl-phenyl-isoeyanate are added and the mixture is warmed for four hours on a water bath, the reaction solution is filtered and the solvent is evaporated. Yield: 17 parts.
The condensation product is dissolved in 3000 parts of 80-85¯ water, mixed with a little animal charcoal and filtered while hot. After adding 65 parts of saturated saline solution, the condensation product separates out. After cooling, it is collected and dried in vacuo. In order to rid it of table salt, it can be extracted from absolute alcohol. After drying and grinding, the new condensation product forms a pale powder that is clearly soluble in hot water.
Example 2:
The 4-chloro-5-trifluoromethyl-phenyl-carbamic acid chloride prepared from phosgene and 4-CMor-5-trifluoromethyl-aniline in a dry, inert solvent gives 2-amino-3 ', 4, 4 with the addition of pyridine as a condensing agent '-triehlor-l, l'-diphenylether-6'-sulfonic acid sodium the urea described in Example lb) in a satisfactory yield.
Example 3:
The 4-chloro-5-trifluoromethyl-phenyl-carbamic acid phenyl ester prepared from chlorocarbonic acid phenyl ester and 4-chloro-5-trifluoromethyl-aniline in dry pvridine gives by reaction with 2-amino-3 ', 4, 4'-triehlor-1, 1' -diphenylether-6'-sulfonic acid sodium in hot water the urea described in Example 1 b); the corresponding methyl ester can also be used instead of the 4-chloro-5-trifluoromethyl-phenyl-carbaminsurephenylesters.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH304943T | 1950-04-29 | ||
| CH300283T | 1950-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH304943A true CH304943A (en) | 1955-01-31 |
Family
ID=25734166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH304943D CH304943A (en) | 1950-04-29 | 1950-04-29 | Process for the production of a condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH304943A (en) |
-
1950
- 1950-04-29 CH CH304943D patent/CH304943A/en unknown
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