Cl[S:2]([NH:5][C:6](=[O:9])[O:7][CH3:8])(=[O:4])=[O:3].[Cl:10][C:11]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([Cl:22])[C:12]=1[NH2:13].C(N(CC)CC)C.O>C(Cl)Cl>[Cl:10][C:11]1[CH:17]=[C:16]([C:18]([F:21])([F:19])[F:20])[CH:15]=[C:14]([Cl:22])[C:12]=1[NH:13][S:2]([NH:5][C:6](=[O:9])[O:7][CH3:8])(=[O:4])=[O:3]Methyl chlorosulfonylcarbamate (27.90 g, 0.16 mol) was dissolved in CH2Cl2 (100 mL) and cooled to −20° C. To the solution of methyl chlorosulfonylcarbamate, was dropwisely added 2,6-dichloro-4-(trifluoromethyl)aniline (2.50 g, 10.7 mmol) and triethylamine (2.53 g, 32.1 mmol) in CH2Cl2 (70 mL) and agitated for 12 hr at room temperature. The reaction mixture was added with water (100 mL) for extraction to obtain the organic layer. The resultant was dried over MgSO4, concentrated under reduced pressure, and purified by column chromatography (hexane:ethyl acetate=7:3), giving the compound of interest (2.11 g, 6%, yellow solid). 1H NMR (300 MHz, CDCl3): δ 7.57 (s, 2H), 3.84 (s, 3H).
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