N-[3-(chloromethyl)phenyl]methanesulfonamide

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

Procedure: 873 mg (4.903 mmol) of 3-(chloromethyl)aniline hydrochloride (Example 89A) were initially charged in 4 ml of tetrahydrofuran, and 2.48 g (24.514 mmol) of triethylamine were added. A solution of 421 mg (3.677 mmol) of methanesulfonyl chloride in 3 ml of tetrahydrofuran was slowly added dropwise, and the reaction solution was stirred at RT for 2 h. The reaction solution was concentrated using a rotary evaporator and the residue was purified by preparative HPLC (Chromasil, water/acetonitrile). The reaction solution was concentrated a rotary evaporator the residue was purified by preparative HPLC (Chromasil, water/acetonitrile)

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

Procedure: A solution of (3-amino-phenyl)-methanol (388 mg, 3.15 mmoles), lithium chloride (270 mg, 6.3 mmoles) and 2,6-lutidine (0.821 mL, 6.93 mmoles) in DMF (10 mL) was cooled at 0° C. under nitrogen atmosphere. Methanesulphonylchloride (0.536 mL, 6.93 mmoles) was added dropwise, and the mixture was stirred at room temperature for 3 hours. Water (30 mL) was then added, and the mixture was extracted with AcOEt (3×40 mL). The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 10/0 to 8/2) to yield 330 mg of the title compound. the mixture was extracted with AcOEt (3×40 mL) The organic layer was washed with brine dried over Na2SO4 evaporated to dryness The crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 10/0 to 8/2)

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

Procedure: 873 mg (4.903 mmol) of 3-(chloromethyl)aniline hydrochloride (Example 89A) were initially charged in 4 ml of tetrahydrofuran, and 2.48 g (24.514 mmol) of triethylamine were added. A solution of 421 mg (3.677 mmol) of methanesulfonyl chloride in 3 ml of tetrahydrofuran was slowly added dropwise, and the reaction solution was stirred at RT for 2 h. The reaction solution was concentrated using a rotary evaporator and the residue was purified by preparative HPLC (Chromasil, water/acetonitrile). The reaction solution was concentrated a rotary evaporator the residue was purified by preparative HPLC (Chromasil, water/acetonitrile)