m-Bromobenzenesulphonyl chloride → HCID 57751032, compound

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([NH2:22])(=[O:21])=[O:20]>N1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([S:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[S:19]([NH2:22])(=[O:20])=[O:21])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

Procedure

3-Bromo-benzenesulfonyl chloride (8.34 mL, 57.9 mmol) was added to a solution of 2-amino-benzenesulfonamide (9.965 g, 57.9 mmol) dissolved in pyridine (90 mL). The reaction was stirred for 4 h followed by solvent removal under vacuo. The reaction mixture was added to water and the product was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated to furnish a dark yellow oil. The oil was dissolved in EtOAc and precipitated by addition of heptane. The solid was finally recrystallized from EtOH to give the title compound (10.784 g, 48%) as a white solid.