DE1261498B - Process for the production of chlorinated phenylcyanamides - Google Patents
Process for the production of chlorinated phenylcyanamidesInfo
- Publication number
- DE1261498B DE1261498B DEF43866A DEF0043866A DE1261498B DE 1261498 B DE1261498 B DE 1261498B DE F43866 A DEF43866 A DE F43866A DE F0043866 A DEF0043866 A DE F0043866A DE 1261498 B DE1261498 B DE 1261498B
- Authority
- DE
- Germany
- Prior art keywords
- chlorinated
- phenylcyanamides
- isocyanide
- production
- nhcn
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- JLXXLCJERIYMQG-UHFFFAOYSA-N phenylcyanamide Chemical class N#CNC1=CC=CC=C1 JLXXLCJERIYMQG-UHFFFAOYSA-N 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- RLAROPIDCNCRNR-UHFFFAOYSA-N Cl.Cl.[C-]#N Chemical class Cl.Cl.[C-]#N RLAROPIDCNCRNR-UHFFFAOYSA-N 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- -1 carbon tetrachloride Chemical class 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- GKFFFNUVYUGXEW-UHFFFAOYSA-N (4-chlorophenyl)cyanamide Chemical compound ClC1=CC=C(NC#N)C=C1 GKFFFNUVYUGXEW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QPPCIPBFKQOIMT-UHFFFAOYSA-N 1-chloro-4-isocyanobenzene Chemical compound ClC1=CC=C([N+]#[C-])C=C1 QPPCIPBFKQOIMT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- RKVTZVIGKJYDTG-UHFFFAOYSA-N (2,5-dichlorophenyl)cyanamide Chemical compound ClC1=CC=C(Cl)C(NC#N)=C1 RKVTZVIGKJYDTG-UHFFFAOYSA-N 0.000 description 1
- VGQKZVPHFLOGTN-UHFFFAOYSA-N (3,4-dichlorophenyl)cyanamide Chemical compound ClC1=CC=C(NC#N)C=C1Cl VGQKZVPHFLOGTN-UHFFFAOYSA-N 0.000 description 1
- PBQDQFPMNAMCRA-UHFFFAOYSA-N 1,1-dichloro-n-(3,4-dichlorophenyl)methanimine Chemical compound ClC(Cl)=NC1=CC=C(Cl)C(Cl)=C1 PBQDQFPMNAMCRA-UHFFFAOYSA-N 0.000 description 1
- TTWWZVGVBRPHLE-UHFFFAOYSA-N 1,1-dichloro-n-phenylmethanimine Chemical compound ClC(Cl)=NC1=CC=CC=C1 TTWWZVGVBRPHLE-UHFFFAOYSA-N 0.000 description 1
- XWTFRFDJAYBRHE-UHFFFAOYSA-N 1,4-dichloro-2-isocyanobenzene Chemical compound ClC1=CC=C(Cl)C([N+]#[C-])=C1 XWTFRFDJAYBRHE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
BUNDESREPUBLIK DEUTSCHLAND DEUTSCHES ^WWS PATENTAMTFEDERAL REPUBLIC OF GERMANY GERMAN ^ WWS PATENT OFFICE
Int. Cl.: Int. Cl .:
Nummer:
Aktenzeichen:
Anmeldetag:
Auslegetag:Number:
File number:
Registration date:
Display day:
C07cC07c
1 261 498
F43866IVb/12o 31. August 1964
22. Februar 19681,261,498
F43866IVb / 12o August 31, 1964 February 22, 1968
Es wurde ein Verfahren zur Herstellung von chlorierten Phenylcyanamiden gefunden, das dadurch gekennzeichnet ist, daß man Isocyaniddichloride, die am Stickstoffatom einen chlorierten Phenylrest, der gegebenenfalls noch durch eine Methylgruppe substituiert sein kann, tragen, mit mindestens 3 Mol Ammoniak je Isocyaniddichloridgruppe in einem inerten organischen Lösungsmittel bei einer Temperatur von 20 bis 250C umsetzt.A process for the preparation of chlorinated phenylcyanamides has been found which is characterized in that isocyanide dichlorides which carry a chlorinated phenyl radical on the nitrogen atom, which may optionally also be substituted by a methyl group, with at least 3 moles of ammonia per isocyanide dichloride group in an inert organic Solvent at a temperature of 20 to 25 0 C converts.
Der überraschende Reaktionsverlauf sei am Beispiel des 4-Chlorphenylisocyaniddichlorids erläutert:The surprising course of the reaction is explained using the example of 4-chlorophenyl isocyanide dichloride:
Verfahren zur Herstellung von chlorierten PhenylcyanamidenProcess for the production of chlorinated phenylcyanamides
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, 5090 LeverkusenPaint factories Bayer Aktiengesellschaft, 5090 Leverkusen
Als Erfinder benannt:Named as inventor:
Dr. Engelbert Kühle, 5070 Bergisch Gladbach; Dr. Bertram Anders, 5000 Köln-StammheimDr. Engelbert Kühle, 5070 Bergisch Gladbach; Dr. Bertram Anders, 5000 Cologne-Stammheim
ClCl
N = CCl,N = CCl,
NH — CN + 2 NH4ClNH - CN + 2 NH 4 Cl
Die für das erfindungsgemäße Verfahren geeigneten Isocyaniddichloride sind am Stickstoffatom substituiert. Als Substituent kommt der chlorierte Phenylrest, welcher gegebenenfalls noch durch eine Methylgruppe substituiert sein kann, in Betracht.The isocyanide dichlorides suitable for the process according to the invention are substituted on the nitrogen atom. The chlorinated phenyl radical, which may also be replaced by a methyl group, is used as a substituent can be substituted into consideration.
Zur Durchführung des erfindungsgemäßen Verfahrens kann man zu 1 Mol Isocyaniddichlorid, z. B. in einem inerten Lösungsmittel, mindestens 3 Mol Ammoniak bei Normaltemperatur einblasen.To carry out the process according to the invention, 1 mol of isocyanide dichloride, z. B. in an inert solvent, blow at least 3 moles of ammonia at normal temperature.
Beispiele inerter Lösungsmittel sind aliphatische und cycloaliphatische Kohlenwasserstoffe, wie Pentan, Hexan, Heptan, Dodecan, Leichtbenzin, Waschbenzin, Cyclohexan, Methylcyclohexan, ferner Halogenkohlenwasserstoffe, wie Tetrachlorkohlenstoff, weiterhin aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Chlorbenzol und Nitrobenzol, sowie Äther, wie Diäthyläther, Dioxan und Tetrahydrofuran. Examples of inert solvents are aliphatic and cycloaliphatic hydrocarbons, such as pentane, Hexane, heptane, dodecane, mineral spirits, petroleum ether, cyclohexane, methylcyclohexane, also halogenated hydrocarbons, such as carbon tetrachloride, also aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and nitrobenzene, and ethers such as diethyl ether, dioxane and tetrahydrofuran.
Die monosubstituierten Cyanamide können als Zwischenprodukte ;zur Herstellung von Pharmazeutika und Pflanzenschutzmitteln verwendet werden.The monosubstituted cyanamides can be used as intermediates; for the manufacture of pharmaceuticals and pesticides are used.
Cl —<^ V- NHCNCl- <^ V- NHCN
In die Lösung von 41 g (0,2 Mol) 4-Chlorphenylisocyaniddichlorid in 250 ml Dioxan leitet man bei 20 bis 25°C 10,5 g (0,62 Mol) Ammoniakgas ein und rührt V2 Stunde lang nach. Man saugt vom ausgefallenen Ammoniumchlorid ab und engt die Lösung ein. Hierbei erhält man 28,5 g 4-Chlorphenylcyanamid vom F. 98 bis 1000C (aus Waschbenzin). 10.5 g (0.62 mol) of ammonia gas are passed into the solution of 41 g (0.2 mol) of 4-chlorophenyl isocyanide dichloride in 250 ml of dioxane at 20 to 25 ° C. and the mixture is stirred for another 2 hours. The precipitated ammonium chloride is filtered off with suction and the solution is concentrated. This gives 28.5 g of 4-chlorophenylcyanamide with a melting point of 98 to 100 ° C. (from petroleum ether).
Berechnet
gefundenCalculated
found
C 55,0, H 3,27, N 18,35; C 54,91, H 3,50, N 18,52.C 55.0, H 3.27, N 18.35; C 54.91, H 3.50, N 18.52.
Beispiel 2 ClExample 2 Cl
ClCl
NHCNNHCN
Nach der im Beispiel 1 beschriebenen Arbeitsweise erhält man bei Verwendung von 3,4-Dichlorphenylisocyaniddichlorid das 3,4-Dichlorphenylcyanamid vom F. 121 bis 124°C. Ausbeute: 80%.Using the procedure described in Example 1, 3,4-dichlorophenyl isocyanide dichloride is obtained 3,4-dichlorophenylcyanamide with a melting point of 121 to 124 ° C. Yield: 80%.
Beispiel 3 ClExample 3 Cl
NHCNNHCN
Nach der im Beispiel 1 beschriebenen Arbeitsweise erhält man bei Verwendung von 2,5-Dichlorphenylisocyaniddichlorid das 2,5-Dichlorphenylcyanamid vom F. 156 bis 158°C. Ausbeute: 63%.Using the procedure described in Example 1, 2,5-dichlorophenyl isocyanide dichloride is obtained 2,5-dichlorophenylcyanamide with a melting point of 156 to 158 ° C. Yield: 63%.
Beispiel 4 Cl CH3 Example 4 Cl CH 3
NHCNNHCN
Arbeitet man entsprechend dem Beispiel 1 unter Verwendung von 2 - Methyl - 3,5 - dichlorphenyl-If you work according to Example 1 using 2 - methyl - 3,5 - dichlorophenyl
809 509/340809 509/340
44th
isocyaniddichlorid, so erhält man in entsprechender weise erhält man bei Verwendung von Pentachlor-Weise das 2-Methyl-3,5-dichlorphenylcyanamid vom phenylisocyaniddichlorid das Pentachlorphenylcyan-F. 146 bis 148°C. Ausbeute: 81%. amid vom F. 275 bis 2800C. Ausbeute: 75%.isocyanide dichloride, the 2-methyl-3,5-dichlorophenylcyanamide of the phenyl isocyanide dichloride, the pentachlorophenylcyan-F, is obtained in a corresponding manner when using the pentachloro mode. 146 to 148 ° C. Yield: 81%. amide with a melting point of 275 to 280 ° C. Yield: 75%.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF43866A DE1261498B (en) | 1964-08-31 | 1964-08-31 | Process for the production of chlorinated phenylcyanamides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF43866A DE1261498B (en) | 1964-08-31 | 1964-08-31 | Process for the production of chlorinated phenylcyanamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1261498B true DE1261498B (en) | 1968-02-22 |
Family
ID=7099764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF43866A Pending DE1261498B (en) | 1964-08-31 | 1964-08-31 | Process for the production of chlorinated phenylcyanamides |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1261498B (en) |
-
1964
- 1964-08-31 DE DEF43866A patent/DE1261498B/en active Pending
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