CA2207583C - Procede de fabrication de 2-(benzoyl substitue)-1,3 cyclohexanediones - Google Patents

Procede de fabrication de 2-(benzoyl substitue)-1,3 cyclohexanediones Download PDF

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Publication number
CA2207583C
CA2207583C CA002207583A CA2207583A CA2207583C CA 2207583 C CA2207583 C CA 2207583C CA 002207583 A CA002207583 A CA 002207583A CA 2207583 A CA2207583 A CA 2207583A CA 2207583 C CA2207583 C CA 2207583C
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CA
Canada
Prior art keywords
alkyl
hydrogen
haloalkyl
alkoxy
independently
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.)
Expired - Fee Related
Application number
CA002207583A
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English (en)
Other versions
CA2207583A1 (fr
Inventor
Stephen Martin Brown
Howard Rawlinson
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Syngenta Participations AG
Original Assignee
Syngenta Ltd
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
Priority claimed from GBGB9501434.6A external-priority patent/GB9501434D0/en
Application filed by Syngenta Ltd filed Critical Syngenta Ltd
Publication of CA2207583A1 publication Critical patent/CA2207583A1/fr
Application granted granted Critical
Publication of CA2207583C publication Critical patent/CA2207583C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

La présente invention concerne la préparation d'un composé représenté par la formule (I) dans laquelle R<1>, R<2>, R<3>, R<4>, R<5> et R<6> sont indépendamment l'hydrogène ou un C1-6alkyle, R<7> est un halogène, cyano, NO2, C1-4alkyle, C1-4haloalkyle, C1-4alkoxy ou RaS où Ra est C1-4alkyle, R<8>, R<9> et R<10> sont indépendamment hydrogène, halogène, C1-4alkyle, C1-4alkoxy, C1-4haloalkyle, C1-4haloalkoxy, CN, NO2, phénoxy ou un phénoxy substitué, RbS(O)n Om où m est égal à 0 ou 1, n est égal à 0, 1 ou 2 et Rb est C1-4alkyle, C1-4haloalkyle, phényle ou benzyle, NHCOR<c> où Rc est C1-4alkyle, NRdRe où Rd et Re sont indépendamment hydrogène ou C1-4alkyle, RfC(O)- où Rf est hydrogène, C1-4alkyle, C1-4haloalkyle ou C1-4alkoxy, SO2NRgRh où Rg et Rh sont indépendamment hydrogène ou C1-4alkyle, ou toute paire d'éléments choisis parmi R<8>, R<9> et R<10>, associée aux atomes de carbone auxquels ils sont fixés, qui forme un cycle hétérocyclique à 5 ou 6 éléments contenant jusqu'à trois hétéroatomes choisis parmi O, N ou S et qui peut être éventuellement substitué par =NOC1-4alkyle, C1-4alkyle, C1-4haloalkyle, C1-4alkoxy, ou un halogène. Ledit procédé comprend également la réorganisation d'un composé représenté par la formule (II) dans laquelle R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, R<9> et R<10> sont tels qu'ils ont été définis pour le composé représenté par la formule (I), cette réorganisation du composé représenté par la formule (II) ayant lieu dans un solvant non polaire en présence d'une source de cyanure, d'un carbonate d'alcali ou de métal alcalino-terreux, d'un catalyseur de transfert de phase et de 1 à 6 moles d'eau.
CA002207583A 1995-01-25 1996-01-16 Procede de fabrication de 2-(benzoyl substitue)-1,3 cyclohexanediones Expired - Fee Related CA2207583C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9501434.6A GB9501434D0 (en) 1995-01-25 1995-01-25 Chemical process
GB9501434.6 1995-01-25
PCT/GB1996/000082 WO1996022958A1 (fr) 1995-01-25 1996-01-16 Procede de fabrication de 2-(benzoyl substitue)-1,3 cyclohexanediones

Publications (2)

Publication Number Publication Date
CA2207583A1 CA2207583A1 (fr) 1996-08-01
CA2207583C true CA2207583C (fr) 2006-12-12

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ID=37561058

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002207583A Expired - Fee Related CA2207583C (fr) 1995-01-25 1996-01-16 Procede de fabrication de 2-(benzoyl substitue)-1,3 cyclohexanediones

Country Status (1)

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CA (1) CA2207583C (fr)

Also Published As

Publication number Publication date
CA2207583A1 (fr) 1996-08-01

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Effective date: 20150116