C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 309/28 (2006.01) C07B 37/04 (2006.01) C07C 303/22 (2006.01) C07C 303/32 (2006.01) C07C 303/38 (2006.01) C07C 311/16 (2006.01) C07D 213/71 (2006.01) C07D 215/36 (2006.01) C07D 239/28 (2006.01) C07D 251/12 (2006.01) C07D 251/16 (2006.01) C07C 309/39 (2006.01)
Patent
CA 2104148
A process for the preparation of substituted benzenes or benzenesulfonic acid and its derivatives comprising diazotisation of an aminobenzene or ortho-amino-benzenesulfonic acid derivative followed by homogeneous palladium-catalysed coupling with an olefin and heterogeneous palladium-catalysed hydrogenation of the olefinic substituent, wherein the homogeneous catalyst is reduced and precipitated as metal after the coupling in the reaction mixture and used as a heterogeneous palladium catalyst for the hydrogenation step. The process is particular suitable for the preparation N-benzenesulfon-N'-triazinyl-urea herbicides. Compounds that can be made by this process are of formula Ia: Ar-CHR a-CHR b R c ~(Ia), wherein R a, R b and R c are independently of each other selected from H; C1-C20alkyl; C1-C20nitriloalkyl; C1-C20hydroxyalkyl; C1-C20halogenalkyl; C1-C12alkyl-COOR d, C1-C12alkyl-CO-NR e R f, C1-C12alkyl-SO2OR d or C1-C12alkyl-SO2-NR e R f, wherein R d, R e and R f independently are H, C1-C12alkyl, phenyl, benzyl or cyclohexyl; C1-C20alkyl-CO; C1-C20alkoxy; C1-C20nitriloalkoxy; C1-C20haolgenalkoxy; C1-C20alkylthio; C1-C20halogenalkylthio; -SO2OR d, -SO2-NR e R f, -COOR d or -CO- NR e R f, wherein R d, R e and R f have the above meanings; halogen; -CN; -NR e R f, wherein R e and R f have the above meanings; phenyl and benzyl; wherein the phenyl and benzyl are unsubstituted or substituted by C1-C20alkyl; C1-C20nitriloalkyl; C1-C20hydroxyalkyl; C1-C20halogenalkyl; C1-C12alkyl-COOR d,~ C1-C12alkyl-CO-NR e R f, C1-C12alkyl-SO2OR d or C1-C12alkyl-SO2-NR e R f, wherein R d, R e and R f have the above meanings; C1-C20alkyl-CO-; C1-C20alkoxy; C1-C20nitriloalkoxy; C1-C20halogenalkoxy; C1-C20alkylthio; C1-C20halogenalkylthio; -SO2OR d, -SO2-NR e R f, -COOR d or -CO-NR e R f, wherein R d, R e and R f have the above meanings; halogen; -CN; or -NR e R f, wherein R e and R f have the above meanings; and wherein R d can also represent -OM or -O (M1)1/2, where M is an alkali metal atom or a tertiary ammonium group, having from 3 to 18 carbon atoms, and M1 is an alkaline earth metal atom; and Ar means C6-C20aryl or C3-C20heteroaryl having 1 to 6 heteroatoms from the group of O, S and N, the aryl and heteroaryl being unsubstituted or substituted by C1-C20alkyl; C1-C20nitriloalkyl; C1-C20hydroxyalkyl; C1-C20halogenalkyl; C1-C12alkyl-COOR d, C1-C12alkyl-CO-NR e R f, C1-C12alkyl-SO2OR d or C1-C12alkyl-SO2-NR e R f, wherein R d, R e and R f have the above meanings; C1-C20alkyl-CO; C1-C20alkoxy; C1-C20nitriloalkoxy; C1-C20halogenalkoxy; C1-C20alkylthio; C1-C20halogenalkylthio; -SO2OR d, -SO2-NR e R f, -COOR d or -CO-NR e R f, wherein R d, R e and R f have the above meanings; halogen; -CN; -NR e R f, wherein R e and R f have the above meanings; -OH or -SH.
Baumeister Peter
Seifert Gottfried
Steiner Heinz
Ag Ciba-Geigy
Fetherstonhaugh & Co.
Syngenta Participations Ag
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