2-(4-bromophenyl)ethanesulfonyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thionyl chloride (1.51 mL, 20.8 mmol) was added dropwise at 0° C. to a suspension of sodium 2-(4-bromo-phenyl)-ethanesulfonate (4.33 g, 15.08 mmol) in a mixture of anhydrous benzene (50 mL) and N,N-dimethylformamide (1 mL). The reaction mixture was allowed to warm to room temperature and was then heated at 80° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through a pad of Celite. The solids were washed with benzene and the combined filtrates were concentrated in vacuo. The residue was taken up in hexane (30 mL) and the resulting suspension was heated at 50° C. for 30 min. After cooling to room temperature, the formed precipitate was collected by filtration to give 4.06 g (95% yield) of the title compound. was then heated at 80° C. for 18 hours The reaction mixture was cooled to room temperature filtered through a pad of Celite The solids were washed with benzene the combined filtrates were concentrated in vacuo the resulting suspension was heated at 50° C. for 30 min After cooling to room temperature the formed precipitate was collected by filtration

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-amino-5-methyl-benzenesulfonamide (0.1 g, 0.53 mmol) and 2-(4-bromo-phenyl)-ethanesulfonyl chloride (0.14 g, 0.49 mmol) in anhydrous pyridine (4 mL) was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (20 mL) and the organic phase was washed with aqueous hydrochloric acid (1 M, 20 mL), saturated sodium bicarbonate (20 mL) and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC, using 5% methanol in dichloromethane as the eluent, to give 80 mg (38% yield) of title compound. the organic phase was washed with aqueous hydrochloric acid (1 M, 20 mL), saturated sodium bicarbonate (20 mL) and brine dried over magnesium sulfate concentrated under reduced pressure The residue was purified by preparative TLC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Thionyl chloride (1.51 mL, 20.8 mmol) was added dropwise at 0° C. to a suspension of sodium 2-(4-bromo-phenyl)-ethanesulfonate (4.33 g, 15.08 mmol) in a mixture of anhydrous benzene (50 mL) and N,N-dimethylformamide (1 mL). The reaction mixture was allowed to warm to room temperature and was then heated at 80° C. for 18 hours. The reaction mixture was cooled to room temperature and filtered through a pad of Celite. The solids were washed with benzene and the combined filtrates were concentrated in vacuo. The residue was taken up in hexane (30 mL) and the resulting suspension was heated at 50° C. for 30 min. After cooling to room temperature, the formed precipitate was collected by filtration to give 4.06 g (95% yield) of the title compound. was then heated at 80° C. for 18 hours The reaction mixture was cooled to room temperature filtered through a pad of Celite The solids were washed with benzene the combined filtrates were concentrated in vacuo the resulting suspension was heated at 50° C. for 30 min After cooling to room temperature the formed precipitate was collected by filtration