[Cl:1][C:2]1[C:18]([N+:19]([O-])=O)=[C:17]([F:22])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][S:7]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])(=[O:9])=[O:8])=[O:5].[Cl-].[NH4+].CO.[H][H]>C1(C)C=CC=CC=1.[Pd]>[Cl:1][C:2]1[C:18]([NH2:19])=[C:17]([F:22])[CH:16]=[CH:15][C:3]=1[C:4]([NH:6][S:7]([N:10]([CH:12]([CH3:14])[CH3:13])[CH3:11])(=[O:9])=[O:8])=[O:5]8.00 g (0.023 mol) of N-(2-chloro-4-fluoro-3-nitrobenzoyl)-N′-isopropyl-N′-methylsulfamide and 70 mg (6 mol %) of ammonium chloride in 33 g of toluene and 8 g of methanol were admixed with 0.19 g (0.15 mol %) of 10% Pd/C and hydrogenated with 5 bar of hydrogen with stirring at 70° C. After 10 h the solution was depressurized, the reaction mixture was filtered and the solvent was removed by distillation. This gave 6.4 g (89%) of the title compound in the form of a solid (m.p.: 147-149° C.).
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