[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=1)[NH2:8])(=[O:4])=[O:3].C(=O)([O-])O.[K+].[Cl:20][CH2:21][C:22](Cl)=[O:23].CC(C)=O.C(OC(C)C)(C)C>C(OCC)(=O)C.O>[Cl:20][CH2:21][C:22]([NH:8][C:7]1[CH:9]=[C:10]([N+:12]([O-:14])=[O:13])[CH:11]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=1)=[O:23]
3-(Methylsulfonyl)-5-nitro-aniline (4.3 g; 19.89 mmol) was diluted in 60 ml of ethyl acetate and a solution of potassium hydrogen carbonate (219 g, 21.87) in 10 ml of water was added. The reaction mixture was stirred at 0° C. and chloroacetylchloride (2.47 ml; 21.87 mmol) was added dropwise. The reaction mixture was allowed to reach room temperature and stirred for 2 h. Then, the phases were separated. The organic phase was dried on MgSO4 and concentrated under vacuum. The oil obtained was treated with acetone/di-isopropyl ether (1/5) and the solid obtained was filtered. 2.5 g (8.54 mmol; 43% yield) of the desired 2-Chloro-N-(3-methanesulfonyl-5-nitro-phenyl)-acetamide were obtained.
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