[NH2:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([CH2:13][Cl:14])(=[O:12])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[Cl:15]N1C(=O)CCC1=O>CN(C)C=O.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([Cl:15])=[C:4]([NH:9][S:10]([CH2:13][Cl:14])(=[O:11])=[O:12])[CH:3]=1A mixture of N-(3-amino-4-fluorophenyl)-1-chloromethanesulfonamide (4.42 g, 18.5 mmol), N-chlorosuccinimide (2.47 g) in 50 mL of anhydrous dimethylformamide was heated to 50° C. for 1.5 hours. The reaction mixture was diluted with 200 mL of ethyl acetate and washed with water (twice with 50 mL). The organic phase was separated, dried (MgSO4), and concentrated under reduced pressure to yield 4.15 g (82%) of the title compound. Purification by flash chromatography provided a solid melting at 107-108° C.
Loading…
