CH306843A - Process for the production of a condensation product. - Google Patents
Process for the production of a condensation product.Info
- Publication number
- CH306843A CH306843A CH306843DA CH306843A CH 306843 A CH306843 A CH 306843A CH 306843D A CH306843D A CH 306843DA CH 306843 A CH306843 A CH 306843A
- Authority
- CH
- Switzerland
- Prior art keywords
- chloro
- trifluoromethyl
- reacted
- aniline
- 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 2
- 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 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- -1 sodium 2 amino-4,5-dichlorobenzenesulphonic acid Chemical compound 0.000 claims description 4
- 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
- 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 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
- 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 1
- 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
- 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
- 239000012948 isocyanate Substances 0.000 description 3
- 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
- 239000002904 solvent Substances 0.000 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 description 1
- AKLDPNVZTZIVFA-UHFFFAOYSA-N 2-azaniumyl-4,5-dichlorobenzenesulfonate Chemical compound NC1=CC(Cl)=C(Cl)C=C1S(O)(=O)=O AKLDPNVZTZIVFA-UHFFFAOYSA-N 0.000 description 1
- WGNNILPYHCKCFF-UHFFFAOYSA-N 2-chloro-n-methylaniline Chemical compound CNC1=CC=CC=C1Cl WGNNILPYHCKCFF-UHFFFAOYSA-N 0.000 description 1
- 101100326319 Mus musculus Brd7 gene Proteins 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
- 150000004651 carbonic acid esters 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
- 239000012442 inert solvent Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 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)
Description
Verfahren zur Herstellung eines Kondensationsproduktes.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung eines Kondensationsproduktes der Formel
EMI1.1
dadurch gekennzeichnet, dass man 3-Trifluor methyl-6-chlor-anilin mit einem Halogenkohlensäurederivat reagieren lässt und das erhal teile reaktive Carbaminsäurederivat mit 2 amino4,5-dichlor-benzolsulfonsaurem Natrium umsetzt.
Eine Ausführungsform des erfindungsge lnässen Verfahrens besteht darin, dass man 3-Tril'luormethyl-6-ehlor-anilin mit Phosgen reagieren lässt und das erhaltene 3-Trifluor methyl-6-ehlor-phenyl-1 - carbaminsäureehlomd mit 2-amino-4, 5-diehlor-benzolsulfonsaurem Natrium umsetzt. Dabei arbeitet man vorzugsweise in Gegenwart einer tertiären Base als Kondensationsmittel. Pyridin oder Chinolin sind für diesen Zweck vor allem geeignet.
Des weiteren kann man 3-Trifluormethyl 6-ehlor-anilin und Phosgen bei erhöhter Temperatur reagieren lassen und das erhaltene n-Triflnormethyl-B- chlor- phenyl-l-isocyanat mit 33-amino-4,5- dichlor- benzolsulfonsaurem Natrium zur Reaktion bringen, wobei man die Verbindung der obigen Formel in guter Aus- beute und vorzüglicher Reinheit erhält. Als Lösungsmittel eignet sieh für diese Art der Umsetzung vor allem Acetonitril oder Pyridin.
Schliesslich besteht eine Ausführungsform darin, dass man 3-Trifluormethyl-6-chlor-ani- lin mit einem llalogenkohlensäureester reagieren lässt und den erhaltenen 3-Trifluormethyl 6-chlor-phenyl-l-carbaminsätreester mit 2amino-4,5-dichlor-benzolsulfonsaurem Natrium umsetzt.
Als Halogenkohlensäureester kommen hauptsächlich niedere Alkyl oder Arylester in Frage. Der Umsatz kann vorteilhaft in Vas- ser vorgenommen werden.
Das neue Kondensationsprodukt bildet ein helles, in heissem Wasser klar lösliches Kri stailpulver, das als Mottensehutzmittel verwendet werden kann.
Beispiel 1 : a) 300 Teile trockenes Benzol werden bei 70" mit Phosgen gesättigt; dazu wird unter Rühren und Einleiten von Phosgen eine Lösung von 100 Teilen 3-Trifluormethyl-6-chloranilin in 300 Teilen trockenem Benzol bei 65 bis 700 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 benzolische Lösung wird hierauf filtriert, das Benzol abdestilliert und das 3-Trifluormethyl 6-chlor-phenyl-l-isocyanat fraktioniert.
Kp75 : 122-1240; Ausbeute 90 Teile. b) 8,8 Teile 2-aniino-4,5-dichlor-beiizolsul- fonsaures Natrium werden in 140 Teilen trokkenem Acetonitril gelöst, mit 7,4 Teilen 3-Tri fluormethyl-6-chlorphenyl-l-isocyanat versetzt und sieben Stunden auf dem Wasserbad erwärmt. Die Reaktionslösung wird filtriert und das Lösungsmittel verdampft. Ausbeute: 11 Teile.
Das neue Kondensationsprodnlrt bildet nach dem Trocknen und Mahlen ein helles, in heissem Wasser klar lösliches Pulver.
Beispiel 2:
Das aus Phosgen und 3-Trifluorinethyl-6- chlor-anilin in einem trockenen inerten Lösungsmittel hergestellte 3- Trifinormethyl -6- chlor - phenyl - 1- carbaminsäureehlorid ergibt unter Zusatz von Pyridin als Kondensationsmittel mit 2 - amino -4,5- diehlor-benzolsulfon- saurem Natrium den in Beispiel 1 b) beschrie- benen Harnstoff in befriedigender Ausbeute.
Beispiel 3:
Der aus Chlorkohlensäurephenylester und 3-Trifluor-methyl-6-chlor-anilin in trockenem Pyridin hergestellte 3-Trifluormethyl-6-chlor- phenyl - 1 - carbaminsäurephenylestcr liefert durch Umsetzung mit 2-amino-4,5-dichlor-ben- zolsulfonsaurem Natrium in heissem Wasser den in Beispiel 1 b) beschriebenen Harnstoff.
Anstatt des 3-Trifluormethyl-6-ehlor-phenyl-1 carbaminsäurephenylesters kann auch der entsprechende Methylester verwendet 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-trifluoro methyl-6-chloro-aniline is allowed to react with a halogenated carbonic acid derivative and the reactive carbamic acid derivative obtained is reacted with 2 amino4,5-dichloro-benzenesulphonic acid sodium.
One embodiment of the process according to the invention consists in allowing 3-trilluoromethyl-6-chloroaniline to react with phosgene and the 3-trifluoro methyl-6-chlorophenyl-1-carbamic acid flouromd with 2-amino-4, 5-diehlor-benzenesulfonic acid sodium converts. It is preferable to work in the presence of a tertiary base as the condensing agent. Pyridine or quinoline are particularly suitable for this purpose.
Furthermore, 3-trifluoromethyl-6-chloro-aniline and phosgene can be allowed to react at elevated temperature and the resulting n-trifluoromethyl-B-chlorophenyl-1-isocyanate can be reacted with sodium 33-amino-4,5-dichlorobenzenesulphonic acid bring, whereby the compound of the above formula is obtained in good yield and excellent purity. Suitable solvents for this type of reaction are above all acetonitrile or pyridine.
Finally, one embodiment consists in reacting 3-trifluoromethyl-6-chloro-aniline with a halogenated carbonic acid ester and allowing the 3-trifluoromethyl 6-chlorophenyl-1-carbamate ester to react with sodium 2 amino-4,5-dichlorobenzenesulfonic acid implements.
Lower alkyl or aryl esters are mainly suitable as halocarbonic acid esters. The conversion can advantageously be carried out 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) 300 parts of dry benzene are saturated with phosgene at 70 "; to this a solution of 100 parts of 3-trifluoromethyl-6-chloroaniline in 300 parts of dry benzene at 65 to 700 is added dropwise while stirring and passing in phosgene 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 3-trifluoromethyl 6-chlorophenyl-1-isocyanate is fractionated.
Bp75: 122-1240; Yield 90 parts. b) 8.8 parts of 2-aniino-4,5-dichloro-bizolsulphonic acid are dissolved in 140 parts of dry acetonitrile, mixed with 7.4 parts of 3-trifluoromethyl-6-chlorophenyl-1-isocyanate and left for seven hours heated in the water bath. The reaction solution is filtered and the solvent is evaporated. Yield: 11 parts.
After drying and grinding, the new condensation product forms a pale powder that is clearly soluble in hot water.
Example 2:
The 3-trifinomethyl-6-chloro-phenyl-1-carbamic acid chloride produced from phosgene and 3-trifluorinethyl-6-chloro-aniline in a dry, inert solvent gives, with the addition of pyridine as a condensing agent with 2-amino -4,5-diehlor- Benzenesulfonic acid sodium, 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-trifluoro-methyl-6-chloro-aniline in dry pyridine, yields by reaction with 2-amino-4,5-dichlorobenzenesulfonic acid sodium in hot water the urea described in Example 1 b).
Instead of the 3-trifluoromethyl-6-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 |
|---|---|---|---|
| CH306843T | 1950-12-26 | ||
| CH300283T | 1950-12-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306843A true CH306843A (en) | 1955-04-30 |
Family
ID=25734232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306843D CH306843A (en) | 1950-12-26 | 1950-12-26 | Process for the production of a condensation product. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306843A (en) |
-
1950
- 1950-12-26 CH CH306843D patent/CH306843A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH306843A (en) | Process for the production of a condensation product. | |
| CH305322A (en) | Process for the production of a condensation product. | |
| CH305314A (en) | Process for the production of a condensation product. | |
| CH304954A (en) | Process for the production of a condensation product. | |
| CH306853A (en) | Process for the production of a condensation product. | |
| CH305317A (en) | Process for the production of a condensation product. | |
| CH305318A (en) | Process for the production of a condensation product. | |
| CH305315A (en) | Process for the production of a condensation product. | |
| CH306851A (en) | Process for the production of a condensation product. | |
| CH306847A (en) | Process for the production of a condensation product. | |
| CH306842A (en) | Process for the production of a condensation product. | |
| CH306856A (en) | Process for the production of a condensation product. | |
| CH305328A (en) | Process for the production of a condensation product. | |
| CH304949A (en) | Process for the production of a condensation product. | |
| CH306845A (en) | Process for the production of a condensation product. | |
| CH306854A (en) | Process for the production of a condensation product. | |
| CH306849A (en) | Process for the production of a condensation product. | |
| CH306852A (en) | Process for the production of a condensation product. | |
| CH306844A (en) | Process for the production of a condensation product. | |
| CH304940A (en) | Process for the production of a condensation product. | |
| CH306855A (en) | Process for the production of a condensation product. | |
| CH304953A (en) | Process for the production of a condensation product. | |
| CH306846A (en) | Process for the production of a condensation product. | |
| CH304955A (en) | Process for the production of a condensation product. | |
| CH306848A (en) | Process for the production of a condensation product. |