[C:1]([C:4]1[CH:10]=[CH:9][C:7](N)=[C:6]([F:11])[CH:5]=1)(=[O:3])[CH3:2].Cl.[N+:13]([O-])([O-])=O.[Na+].[S:18](=[O:20])=[O:19]>O.C(O)(=O)C.O.O.[Cu](Cl)Cl>[C:1]([C:4]1[CH:10]=[CH:9][C:7]([S:18]([NH2:13])(=[O:20])=[O:19])=[C:6]([F:11])[CH:5]=1)(=[O:3])[CH3:2]
To a solution of 4-acetyl-2-fluoroaniline (5.0 g, 32.6 mmol, Krueger, G et al., Arzneim Forsch, 34, 11a, 1612 (1984)) in conc-HCl (24.0 mL), sodium nitrate (2.9 g, 42.4 mmol) in water (10 mL) was added at 0° C. After stirring for 1 h, the resultant yellow solution was added slowly to the suspension of copper (II) chloride dihydrate (1.7 g, 9.8 mmol) and sulfur dioxide (10 g, 156 mmol) in acetic acid (25 mL) at 0° C. The mixture was stirred for 30 min at 0° C. and poured into ice water (200 mL) and extracted with CH2Cl2 (80 mL×2). The extracts was cooled to 0°0 C. and 25% aqueous ammonia (70 mL) was added slowly and stirred for 1 h at room temperature. The mixture was concentrated and the residual solid was suspended with ether and collectted by filteration to give the title compound (3.3 g, 46%).
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