4-(bromomethyl)-N-methylbenzenesulfonamide

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

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

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

Procedure: Mix 4-(bromomethyl)benzenesulfonyl chloride (2.7 g, 10 mmol), anhydrous potassium carbonate (1.4 g, 10 mmol) and anhydrous THF (60 mL) under nitrogen. Cool the mixture in an ice bath, add dropwise a 2M solution of methylamine in THF, and stir at this temperature for 30 min. Remove the ice bath and stir at ambient temperature for 16 h. Dilute with EtOAc then wash with 1N aqueous HCl. Separate the organic layer, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7) to obtain the title compound (1.5 g, 71%). MS (ES+) m/z: 266 (M+H)+. Cool the mixture in an ice bath Remove the ice bath stir at ambient temperature for 16 h Dilute with EtOAc then wash with 1N aqueous HCl Separate the organic layer dry over Na2SO4 concentrate in vacuo Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7)

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

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

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred room temperature solution of 4-bromomethyl-N-methyl-benzenesulfonamide (2.70 g, 10.0 mmol) in DMF (15 mL) was added sodium azide (0.90 g, 13 mmol). The mixture was stirred at 40° C. for 16 hours. The solution was poured into water (60 mL) and diluted with ethyl acetate (100 mL). The organic layer was separated and washed with brine (30 mL), dried over sodium sulfate and concentrated in vacuo to afford 4-azidomethyl-N-methyl-benzenesulfonamide. The organic layer was separated washed with brine (30 mL) dried over sodium sulfate concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a chilled (0° C.) stirred solution of 4-(bromomethyl)-benzenesulfonylchloride (3.0 g, 11 mmol) in DCM (100 mL) was added methylamine hydrochloride (1.2 g, 12 mmol). After 30 minutes, water (100 mL) was added. The organic layer was separated, washed with brine (30 mL), and dried over sodium sulfate and concentrated in vauco to afford 4-bromomethyl-N-methyl-benzenesulfonamide. The organic layer was separated washed with brine (30 mL) dried over sodium sulfate concentrated in vauco

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a chilled (0° C.) stirred solution of 4-(bromomethyl)-benzenesulfonylchloride (3.0 g, 11 mmol) in DCM (100 mL) was added methylamine hydrochloride (1.2 g, 12 mmol). After 30 minutes, water (100 mL) was added. The organic layer was separated, washed with brine (30 mL), and dried over sodium sulfate and concentrated in vauco to afford 4-bromomethyl-N-methyl-benzenesulfonamide. The organic layer was separated washed with brine (30 mL) dried over sodium sulfate concentrated in vauco

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a chilled (0° C.) stirred solution of 4-(bromomethyl)-benzenesulfonylchloride (3.0 g, 11 mmol) in DCM (100 mL) was added methylamine hydrochloride (1.2 g, 12 mmol). After 30 minutes, water (100 mL) was added. The organic layer was separated, washed with brine (30 mL), and dried over sodium sulfate and concentrated in vauco to afford 4-bromomethyl-N-methyl-benzenesulfonamide. The organic layer was separated washed with brine (30 mL) dried over sodium sulfate concentrated in vauco

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

Procedure: Mix 4-(bromomethyl)benzenesulfonyl chloride (2.7 g, 10 mmol), anhydrous potassium carbonate (1.4 g, 10 mmol) and anhydrous THF (60 mL) under nitrogen. Cool the mixture in an ice bath, add dropwise a 2M solution of methylamine in THF, and stir at this temperature for 30 min. Remove the ice bath and stir at ambient temperature for 16 h. Dilute with EtOAc then wash with 1N aqueous HCl. Separate the organic layer, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7) to obtain the title compound (1.5 g, 71%). MS (ES+) m/z: 266 (M+H)+. Cool the mixture in an ice bath Remove the ice bath stir at ambient temperature for 16 h Dilute with EtOAc then wash with 1N aqueous HCl Separate the organic layer dry over Na2SO4 concentrate in vacuo Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7)

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred room temperature solution of 4-bromomethyl-N-methyl-benzenesulfonamide (2.70 g, 10.0 mmol) in DMF (15 mL) was added sodium azide (0.90 g, 13 mmol). The mixture was stirred at 40° C. for 16 hours. The solution was poured into water (60 mL) and diluted with ethyl acetate (100 mL). The organic layer was separated and washed with brine (30 mL), dried over sodium sulfate and concentrated in vacuo to afford 4-azidomethyl-N-methyl-benzenesulfonamide The organic layer was separated washed with brine (30 mL) dried over sodium sulfate concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a chilled (0° C.) stirred solution of 4-(bromomethyl)-benzenesulfonylchloride (3.0 g, 11 mmol) in DCM (100 mL) was added methylamine hydrochloride (1.2 g, 12 mmol). After 30 minutes, water (100 mL) was added. The organic layer was separated, washed with brine (30 mL), and dried over sodium sulfate and concentrated in vacuo to afford 4-bromomethyl-N-methyl-benzenesulfonamide. The organic layer was separated washed with brine (30 mL) dried over sodium sulfate concentrated in vacuo