C[N-:2][S:3](=[O:9])(=[O:8])[NH:4][CH:5]([CH3:7])[CH3:6].[OH-].[Na+].[Cl:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20]([F:25])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].[CH3:26]CCC(C)C.Cl>[Cl-].C([N+](CCCC)(CCCC)C)CCC.ClC1C=CC=CC=1.O>[Cl:12][C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[C:20]([F:25])[CH:19]=[CH:18][C:14]=1[C:15]([NH:2][S:3]([N:4]([CH:5]([CH3:7])[CH3:6])[CH3:26])(=[O:9])=[O:8])=[O:16]
A solution of 43.1 g (0.277 mol) of N-methyl-N-(1-methylethyl)sulfamoylamide and 0.77 g (12.0 mmol) of tributylmethylammonium chloride in 637 g of chlorobenzene was admixed over the course of 60 min at 20° C. with 43.7 g (50% in water) of NaOH. After the base had been added for 15 minutes, a parallel addition commenced of 65.0 g (0.26 mol) of 2-chloro-4-fluoro-3-nitrobenzoyl chloride in 70 g of chlorobenzene. This addition took place over the course of 45 min. The reaction mixture was subsequently stirred at 20° C. for 1 h and diluted by addition of 424 g of water and 138 g of isohexane. The aqueous phase was acidified to a pH of 4.5 using concentrated hydrochloric acid and then separated off at 68° C. The organic phase was extracted a second time with addition of 430 g of water and 60 g of isohexane, and the phases were separated at 68° C. The resulting organic phase was admixed with a further 280 g of isohexane and then cooled to 0° C. Filtration, washing with water and drying under reduced pressure at 70° C. gave 82.1 g (87% of theory, purity 97%) of N-(2-chloro-4-fluoro-3-nitrobenzoyl)-N′-isopropyl-N′-methylsulfamide. In the solid, HPLC analysis found no contamination with 2-chloro-4-fluoro-3-nitrobenzoic acid.
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