Patent EP-1911748-B1 (EP)
Inventor: VERMEHREN JAN DR
IPC: C07C303/38
Filed: 2000-09-28
Granted: 2010-04-07
Abstract: N 1>-Phenylsulfonyl-N 2>-(pyrimidinyl or triazinyl)-urea derivatives are produced from phenylsulfonyl halides by ammonolysis, reaction of the resulting phenylsulfonamides with phosgene and condensation of the phenylsulfonyl isocyanates obtained with an aminopyrimidine or aminotriazole; selected solvent mixtures are used for the ammonolysis and/or condensation. Production of N 1>-phenylsulfonyl-N 2>-(pyrimidinyl or triazinyl)-urea derivatives comprises: (a) ammonolysis of a phenylsulfonyl halide (II) with ammonia, preferably (a1) in a solvent mixture comprising a 20:1 to 1:1, preferably 10:1-1.4:1, by weight mixture of optionally halogenated aromatic hydrocarbon(s) and polar aprotic solvent(s); (b) reaction of the resulting phenylsulfonamide (III) (with or without isolation) with phosgene, preferably (b1) in an organic solvent in the presence of a catalyst comprising isocyanate(s) of the formula R'-NCO (R = optionally substituted hydrocarbyl) and optionally a co-catalyst comprising an amine base; and (c) condensation of the phenylsulfonyl isocyanate (IV) obtained (with or without isolation) with an aminopyrimidine or aminotriazole (V) in an organic solvent; preferably (c1) in a solvent mixture comprising an optionally halogenated hydrocarbon of b.pt. above 110[deg]C and a polar aprotic solvent; provided that steps (a) and/or (c ) are carried out according to (a1) and/or (c1), respectively. [Image] Q : O; S; or N(R 4>); X* : H; halo; CN; NO 2; 1-3C alkyl; or OCH 3; X and Y : CH or N, but are not both CH; R : H; 1-12C alkyl; 2-10C alkenyl; 2-10C alkynyl; 1-6C alkyl substituted with 1-4 halo, 1-4C alkoxy, 1-4C alkylthio, CN, 1-4C alkoxy-CO and/or 2-6C alkenyl; 3-8C cycloalkyl optionally substituted with 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio and/or halo; 5-8C cycloalkenyl; phenyl-1-4C alkyl optionally ring-substituted with 1 or more halo, 1-4C alkyl, 1-4C alkoxy, 1-4C haloalkyl, 1-4C alkylthio, 1-4C alkoxy-CO, 1-4C alkyl-CO-O, CONH 2, 1-4C alkyl-CO-NH, 1-4C alkyl-NH-CO, (1-4C alkyl) 2N-CO and/or NO 2; 2-oxo-1,3-dioxolan-5-ylmethyl; 2,2-dimethyl-1,3-dioxolan-5-ylmethyl; 1,3-dioxolan-2-ylmethyl; or a group of formula (A-1)-(A-5): X : O; S; SO; or SO 2 and X 1> = CH 2; or X : CH 2 and X 1> = O; S; SO; or SO 2; X 2>O; S; SO; or SO 2; R 1>H or 1-3C alkyl; R 2>H; halo; or 1-3C alkyl or 1-3C alkoxy (both optionally substituted with 1 or more halo or 1-3C alkoxy); R 3>H; halo; 1-3C alkyl, 1-3C alkoxy or 1-3C alkylthio (each optionally substituted with 1 or more halo or optionally substituted with one or two 1-3C alkoxy or 1-3C alkylthio); NR 5>R 6>; 3-6C cycloalkyl; 2-4C alkenyl; 2-4C alkynyl; 3-4C alkenyloxy; or 3-4C alkynyloxy; R 4>H; 1-4C alkyl; or 1-4C alkoxy; R 5> and R 6>H; 1-4C alkyl; 3-4C alkenyl; 1-4C haloalkyl; or 1-4C alkoxy. Independent claims are also included for: (A) step (a) carried out under conditions (a1); (B) step (b) carried out using a phenylsulfonamide (III) with X* = halo and carried out under conditions (b1) (the co-catalyst can be a base other than an amine base); and (C) step (c) carried out under conditions (c1).