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WO1996012707A1 - 2-chloro-n-[1-(2,6-dichloro-4-difluoromethyl-phenyl)-1h-pyrazol-5-yl]-propanamide et son procede de fabrication - Google Patents

2-chloro-n-[1-(2,6-dichloro-4-difluoromethyl-phenyl)-1h-pyrazol-5-yl]-propanamide et son procede de fabrication Download PDF

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Publication number
WO1996012707A1
WO1996012707A1 PCT/EP1995/004000 EP9504000W WO9612707A1 WO 1996012707 A1 WO1996012707 A1 WO 1996012707A1 EP 9504000 W EP9504000 W EP 9504000W WO 9612707 A1 WO9612707 A1 WO 9612707A1
Authority
WO
WIPO (PCT)
Prior art keywords
dichloro
pyrazol
phenyl
difluoromethyl
chloro
Prior art date
Application number
PCT/EP1995/004000
Other languages
German (de)
English (en)
Inventor
Hans-Joachim Knops
Bernd Gallenkamp
Lothar Rohe
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to EP95936468A priority Critical patent/EP0788484A1/fr
Priority to AU38408/95A priority patent/AU3840895A/en
Publication of WO1996012707A1 publication Critical patent/WO1996012707A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/38—Nitrogen atoms
    • C07D231/40—Acylated on said nitrogen atom

Definitions

  • the invention relates to the new compound 2-chloro-N- [1- (2,6-dichloro-4-difluoromethylphenyl) -1H-pyrazol-5-yl] propanamide and a process for its preparation.
  • novel compound of the formula (I) can be obtained in the yield according to the invention in considerably higher yield than in the case of synthesis carried out analogously (cf. EP-A 303153).
  • the method according to the invention thus represents a valuable addition to the prior art.
  • the compound 3- [2- (2,6-dichloro-4-trifluoromethylphenyl) hydrazino] propane nitrile of the formula (II) to be used as starting material in the process according to the invention is known and can be prepared by a known process (see EP-A 303 53).
  • the process according to the invention is preferably carried out in the first stage in the presence of a suitable base.
  • suitable bases include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, lithium, sodium, potassium or calcium hydride, lithium, sodium or Potassium amide, sodium or potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide, ammonium hydroxide, sodium, Potassium or calcium acetate, ammonium acetate, sodium, potassium or calcium carbonate, ammonium carbonate, sodium or potassium hydrogen carbonate, and basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N- Dimethylcycl
  • Alkali metal hydroxides e.g. Sodium hydroxide or potassium hydroxide, or alkali metal alcoholates such as e.g. Sodium or potassium methanolate, ethanolate, n or i
  • Suitable diluents for carrying out the first stage of the process according to the invention are the customary organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, Toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl - or diethyl ether, diethylene glycol dimethyl ether or diethyl ether, ketones such as
  • Alcohols e.g. Methanol, ethanol, n- or i-propanol are particularly preferred as diluents when carrying out the first stage of the process according to the invention.
  • the first stage of the process according to the invention is carried out under an inert gas atmosphere.
  • the usual inert gases preferably nitrogen or argon, are suitable here.
  • reaction temperatures can be varied within a substantial range when carrying out the first stage of the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 10 ° C and 120
  • the first stage of the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the starting compound of the formula (II) is placed in a suitable diluent and the air present in the reaction vessel is then replaced by an inert gas, preferably at elevated temperature. Then a base - preferably dissolved in a diluent such as water or one of the abovementioned alcohols and preferably treated with an inert gas before the addition - is metered in and the reaction mixture is stirred at the required temperature under an inert gas atmosphere until the reaction has ended.
  • a suitable diluent such as water or one of the abovementioned alcohols and preferably treated with an inert gas before the addition - is metered in and the reaction mixture is stirred at the required temperature under an inert gas atmosphere until the reaction has ended.
  • the compound of the formula (III) - can be carried out in the customary manner.
  • the mixture is diluted to 2 to 5 times the volume with water and, after stirring for a long time with cooling, the crystalline product is isolated by suction. It can be further purified by recrystallization, for example from xylene / cyclohexane.
  • the second stage of the process according to the invention is preferably carried out in the presence of a suitable acid acceptor.
  • a suitable acid acceptor All customary organic or organic bases are suitable as such. These include, for example, alkali metal or alkaline earth metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, lithium, sodium, potassium or calcium hydride, lithium, sodium - or potassium amide, sodium or potassium methylate, sodium or potassium ethylate, sodium or potassium propylate, aluminum isopropylate, sodium or potassium tert-butoxide, sodium or potassium hydroxide, ammonium hydroxide, sodium -, potassium or calcium acetate, ammonium acetate, sodium, potassium or calcium carbonate, ammonium carbonate, sodium or potassium hydrogen carbonate, and also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropy
  • Py ⁇ din is particularly preferred as an acid acceptor
  • the customary organic solvents are suitable as diluents for carrying out the second stage of the process according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, Xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane, chloroform, carbon tetrachloride, ethers, such as diethyl ether, diisopropyl ether, t-butyl methyl ether, t-pentyl methyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl or diethyl glycol, diethyl ether - Dimethyl ether or diethyl ether, ketones,
  • reaction temperatures can be varied within a substantial range. In general, temperatures between -20 ° C. and + 100 ° C., preferably at temperatures between 0 ° C. and 100 ° C.
  • the second stage of the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar
  • 1 - (2,6-di-chloro-4-difluoromethyl-phenyl) -1H-pyrazole-5-amine of the formula (III) is used per mole generally 1.0 to 1.5 moles, preferably 1.05 to 1.2 moles of 2-chloropropionic acid chloride.
  • the compound of the formula (III) is placed in a suitable diluent and an acid acceptor is added.
  • the 2-chloropropionic acid chloride is then slowly metered in and the reaction mixture is stirred until the reaction has ended.
  • the compound of formula (I) - can be carried out in a conventional manner. For example, it is diluted to 2 to 5 times the volume with water and, after stirring for a long time, the crystalline product is isolated by suction
  • the compound of the formula (I) to be prepared by the process according to the invention can be used as starting material for the preparation of the herbicidally active compound 2-chloro-N- [l- (2,6-dichloro-4-difluoromethyl-phenyl) -4-nitro-1H- pyrazol-5-yl] propanamide (cf. EP-A 303153) can be used according to the following formula:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne le nouveau composé 2-chloro-N-[1-(2,6-dichloro-4-difluorométhyl-phényl)-1H-pyrazol-5-yl]-propanamide de formule (I), un procédé de fabrication de ce composé, ainsi que son utilisation comme produit de départ pour la fabrication du composé herbicide 2-chloro-N-[1-(2,6-dichloro-4-difluorométhyl-phényl)-4-nitro-1H-pyrazol-5-yl]-propanamide de formule (II) ci-après.
PCT/EP1995/004000 1994-10-24 1995-10-11 2-chloro-n-[1-(2,6-dichloro-4-difluoromethyl-phenyl)-1h-pyrazol-5-yl]-propanamide et son procede de fabrication WO1996012707A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP95936468A EP0788484A1 (fr) 1994-10-24 1995-10-11 2-chloro-n- 1-(2,6-dichloro-4-difluoromethyl-phenyl)-1h-pyrazol-5-yl]-propanamide et son procede de fabrication
AU38408/95A AU3840895A (en) 1994-10-24 1995-10-11 2-chloro-n-{1-(2,6-dichloro-4-difluoromethyl-phenyl) -1h-pyrazol-5-yl}-propanamide and a method of producing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4437930.7 1994-10-24
DE19944437930 DE4437930A1 (de) 1994-10-24 1994-10-24 2-Chlor-N-[1-(2,6-dichlor-4-difluormethyl- phenyl)-1H-pyrazol-5-yl]-propanamid

Publications (1)

Publication Number Publication Date
WO1996012707A1 true WO1996012707A1 (fr) 1996-05-02

Family

ID=6531542

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/004000 WO1996012707A1 (fr) 1994-10-24 1995-10-11 2-chloro-n-[1-(2,6-dichloro-4-difluoromethyl-phenyl)-1h-pyrazol-5-yl]-propanamide et son procede de fabrication

Country Status (4)

Country Link
EP (1) EP0788484A1 (fr)
AU (1) AU3840895A (fr)
DE (1) DE4437930A1 (fr)
WO (1) WO1996012707A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0303153A2 (fr) * 1987-08-13 1989-02-15 Bayer Ag Aryl-1-pyrazoles

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0303153A2 (fr) * 1987-08-13 1989-02-15 Bayer Ag Aryl-1-pyrazoles

Also Published As

Publication number Publication date
DE4437930A1 (de) 1996-04-25
AU3840895A (en) 1996-05-15
EP0788484A1 (fr) 1997-08-13

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