2-chloro-5-(hydroxymethyl)benzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a well stirred solution of 2-chloro-5-hydroxymethyl-benzenesulfonamide (31.6 g, 143 mmol) in 300 mL tetrahydrofuran is added 62.0 g (713 mmol) of MnO2. The resulting solution is heated at reflux for 16 h, filtered through Celite then through a 0.4 μM Teflon filter and the filtrate is concentrated in vacuo to remove the tetrahydrofuran. Trituration with hexanes provided 25 g (80%) of the title compound as a grey solid. The resulting solution is heated at reflux for 16 h filtered through Celite through a 0.4 μM Teflon filter the filtrate is concentrated in vacuo to remove the tetrahydrofuran

Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chloro-3-sulfamoyl-benzoic acid ethyl ester (46.95 g, 166 mmol) in 500 mL of dry tetrahydrofuran is added dropwise, with stirring, 199 mL of a 2 M solution of lithium borohydride in tetrahydrofuran. The mixture is stirred and refluxed for 5 hr, then left at room temperature for 18 h, and is then carefully diluted with 400 mL of water. The mixture is cooled to 4° C. for 24 hours and filtered to yield 32.7 g (82%) of the title compound as an off-white solid. The mixture is stirred refluxed for 5 hr filtered

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

Procedure: A solution of 2-chloro-5-(hydroxymethyl)benzenesulfonamide (696 mg, 3.14 mmol) in acetone (30 mL) was added to a round bottom flask containing MnO2 (2.73 g, 31.4 mmol). The mixture was stirred for 50 hours until the starting material was consumed, then filtered though a pad of celite. The filtrate was evaporated to afford the product (444 mg, 64%) as a white solid. MS (ES+) m/z 220 [M+H]+. was consumed filtered though a pad of celite The filtrate was evaporated

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

Procedure: To a solution of methyl 3-(aminosulfonyl)-4-chlorobenzoate (950 mg, 3.8 mmol) in THF/EtOH (40 mL, 1:1), CaCl2 (843 mg, 7.6 mmol) and NaBH4 (575 mg, 15.2 mmol) were added in one portion respectively. The reaction mixture was stirred at room temperature for 6 hours, then quenched with water. 1 M aqueous citric acid (10 mL) was added to the mixture and extracted with EtOAc (3×100 mL). The extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated to afford the product (696 mg, 83%) as a white solid. MS (ES+) m/z 244 [M+Na]+. quenched with water 1 M aqueous citric acid (10 mL) was added to the mixture extracted with EtOAc (3×100 mL) washed with brine dried (Na2SO4) The solvent was evaporated

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

Procedure: To a solution of methyl 3-(aminosulfonyl)-4-chlorobenzoate (950 mg, 3.8 mmol) in THF/EtOH (40 mL, 1:1), CaCl2 (843 mg, 7.6 mmol) and NaBH4 (575 mg, 15.2 mmol) were added in one portion respectively. The reaction mixture was stirred at room temperature for 6 hours, then quenched with water. 1 M aqueous citric acid (10 mL) was added to the mixture and extracted with EtOAc (3×100 mL). The extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated to afford the product (696 mg, 83%) as a white solid. MS (ES+) m/z 244 [M+Na]+. quenched with water 1 M aqueous citric acid (10 mL) was added to the mixture extracted with EtOAc (3×100 mL) washed with brine dried (Na2SO4) The solvent was evaporated

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a well stirred solution of 2-chloro-5-hydroxymethyl-benzenesulfonamide (31.6 g, 143 mmol) in 300 mL tetrahydrofuran is added 62.0 g (713 mmol) of MnO2. The resulting solution is heated at reflux for 16 h, filtered through Celite then through a 0.4 μM Teflon filter and the filtrate is concentrated in vacuo to remove the tetrahydrofuran. Trituration with hexanes provided 25 g (80%) of the title compound as a grey solid. The resulting solution is heated at reflux for 16 h filtered through Celite through a 0.4 μM Teflon filter the filtrate is concentrated in vacuo to remove the tetrahydrofuran

Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chloro-3-sulfamoyl-benzoic acid ethyl ester (46.95 g, 166 mmol) in 500 mL of dry tetrahydrofuran is added dropwise, with stirring, 199 mL of a 2 M solution of lithium borohydride in tetrahydrofuran. The mixture is stirred and refluxed for 5 hr, then left at room temperature for 18 h, and is then carefully diluted with 400 mL of water. The mixture is cooled to 4° C. for 24 hours and filtered to yield 32.7 g (82%) of the title compound as an off-white solid. The mixture is stirred refluxed for 5 hr filtered

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

Procedure: To a well stirred solution of 2-chloro-5-hydroxymethyl-benzenesulfonamide (31.6 g, 143 mmol) in 300 mL tetrahydrofuran is added 62.0 g (713 mmol) of MnO2. The resulting solution is heated at reflux for 16 h, filtered through Celite then through a 0.4 μM Teflon filter and the filtrate is concentrated in vacuo to remove the tetrahydrofuran. Trituration with hexanes provided 25 g (80%) of the title compound as a grey solid. The resulting solution is heated at reflux for 16 h filtered through Celite through a 0.4 μM Teflon filter the filtrate is concentrated in vacuo to remove the tetrahydrofuran

Conditions: temp:4.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-chloro-3-sulfamoyl-benzoic acid ethyl ester (46.95 g, 166 mmol) in 500 mL of dry tetrahydrofuran is added dropwise, with stirring, 199 mL of a 2 M solution of lithium borohydride in tetrahydrofuran. The mixture is stirred and refluxed for 5 hr, then left at room temperature for 18 h, and is then carefully diluted with 400 mL of water. The mixture is cooled to 4° C. for 24 hours and filtered to yield 32.7 g (82%) of the title compound as an off-white solid. The mixture is stirred refluxed for 5 hr filtered

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

Procedure: To a well stirred solution of 2-chloro-5-hydroxymethyl-benzenesulfonamide (31.6 g, 143 mmol) in 300 mL tetrahydrofuran is added 62.0 g (713 mmol) of MnO2. The resulting solution is heated at reflux for 16 h, filtered through Celite then through a 0.4 μM Teflon filter and the filtrate is concentrated in vacuo to remove the tetrahydrofuran. Trituration with hexanes provided 25 g (80%) of the title compound as a grey solid. The resulting solution is heated at reflux for 16 h filtered through Celite through a 0.4 μM Teflon filter the filtrate is concentrated in vacuo to remove the tetrahydrofuran