Process for preparing herbicidal sulfonamides

Details Process for preparing herbicidal sulfonamides Process for preparing herbicidal sulfonamides

C - Chemistry, Metallurgy

07

D

260/259, 260/242

C07D 403/12 (2006.01) C07D 491/044 (2006.01)

Patent

CA 1204743

ABSTRACT OF THE DISCLOSURE A process for preparing pyrrole sulfonamides of the formula Image or Image Ia Ib which are useful as agricultural chemicals, by reacting under reaction conditions in a solvent, in the presence of a Friedel-Crafts catalyst, Image and Image (II) (III) wherein R1 is H, C1-C4 alkyl, NO2, CN, C(0)CC13, SO2R11, C(0)R5 or CO2H; R2 is H or C1-C4 alkyl; R3 is H, C1-C4 alkyl, Cl or Br; R4 is H, C1-C4 alkyl, cyanoethyl, C5-C6 cycloalkyl, benzyl, phenyl substituted with Cl or NO2, or C(O) R6; R5 is C1-C4 alkyl or C1-C4 alkoxy; R6 is C1-C4 alkyl, C1-C4 alkoxy, or NR7R8; R7 and R8 are independently C1-C2 alkyl; R9 is H, CH3 or OCH3; R11 is C1-C4 alkyl; R10 is Image Image ; X is CH3 or OCH3; Y is H, CH3, OCH3, OCH2CH3, OCH2CF3, Cl, CH2OCH3, CH2OCH2CH3 or CF3; Y1 is H, CH3, OCH3, Cl or OCH2CH3; and Z is CH, N, CCH3 CCH2CH3, CCH2CH2Cl, CCl, CBr or CF; provided that (1) when R4 is C(O)R6, t-butyl or phenyl substituted with Cl or NO2, then R1 is H or C1-C4 alkyl and R1, R2 and R3 cannot be s-butyl or isopropyl; (2) R1, R2, R3 and R11 cannot be t-butyl; (3) in Formula Ia, when R1 is NO2, then R1 cannot be in the 5-position; (4) in Formula Ia, when R1 is not in the 5-position and R2 and R3 are other than H then R1 must be other than H; (5) in Formula Ia, R3 cannot be Cl or Br; (6) in Formula Ib, R1 cannot be C(O)CCl3; and (7) in Formula Ib, when R3 is Cl or Br, then R3 is in the 3-position and R1 is in the 5-position and R1 cannot be H or C1-C4 alkyl.

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