2-(benzenesulfonylmethyl)aniline

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

Procedure: A stirred solution of 2-[(phenylsulfonyl)methyl]aniline (247 mg, 1.00 mmol) in 4N HCl (50 ml) is treated with a solution of NaNO2 (100 mg, 1.5 mmol) in water at ice-bath temperatures, stirred for 30 min., neutralized with 10% NaOH and filtered. The filtercake is dissolved in CH2Cl2, dried over MgSO4 and concentrated in vacuo to afford the title product as a tan solid, 240 mg (93% yield), mp 118° C., identified by mass spectral and HNMR analyses. filtered The filtercake is dissolved in CH2Cl2 dried over MgSO4 concentrated in vacuo

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

Procedure: A stirred solution of 2-[(phenylsulfonyl)methyl]aniline (247 mg, 1.00 mmol) in 4N HCl (50 ml) is treated with a solution of NaNO2 (100 mg, 1.5 mmol) in water at ice-bath temperatures, stirred for 30 min., neutralized with 10% NaOH and filtered. The filtercake is dissolved in CH2Cl2, dried over MgSO4 and concentrated in vacuo to afford the title product as a tan solid, 240 mg (93% yield), mp 118° C., identified by mass spectral and HNMR analyses. filtered The filtercake is dissolved in CH2Cl2 dried over MgSO4 concentrated in vacuo

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 2-(phenylsulfonylmethyl)-1-nitrobenzene (5.55 g, 20.0 mmol) and granular tin (10.4 g, 88 mmol) in methanol and concentrated HCl (60 mL) is stirred under nitrogen at 45° C. for 5 h, cooled to ambient temperature over an 18 h period, poured onto NaHCO3 (80 g) with stirring, treated with water and extracted with ethyl acetate. The combined extracts are washed with brine (2×100 mL), dried over MgSO4, and concentrated in vacuo to afford the title product as an off-white solid, 4.41 g (89%) mp 175–176° C., identified by HNMR and mass spectral analyses. cooled to ambient temperature over an 18 h period poured onto NaHCO3 (80 g) with stirring extracted with ethyl acetate The combined extracts are washed with brine (2×100 mL) dried over MgSO4 concentrated in vacuo

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 2-(phenylsulfonylmethyl)-1-nitrobenzene (5.55 g, 20.0 mmol) and granular tin (10.4 g, 88 mmol) in methanol and concentrated HCl (60 mL) is stirred under nitrogen at 45° C. for 5 h, cooled to ambient temperature over an 18 h period, poured onto NaHCO3 (80 g) with stirring, treated with water and extracted with ethyl acetate. The combined extracts are washed with brine (2×100 mL), dried over MgSO4, and concentrated in vacuo to afford the title product as an off-white solid, 4.41 g (89%) mp 175–176° C., identified by HNMR and mass spectral analyses. cooled to ambient temperature over an 18 h period poured onto NaHCO3 (80 g) with stirring extracted with ethyl acetate The combined extracts are washed with brine (2×100 mL) dried over MgSO4 concentrated in vacuo

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

Procedure: A stirred solution of 2-[(phenylsulfonyl)methyl]aniline (247 mg, 1.00 mmol) in 4N HCl (50 ml) is treated with a solution of NaNO2 (100 mg, 1.5 mmol) in water at ice-bath temperatures, stirred for 30 min., neutralized with 10% NaOH and filtered. The filtercake is dissolved in CH2Cl2, dried over MgSO4 and concentrated in vacuo to afford the title product as a tan solid, 240 mg (93% yield), mp 118° C., identified by mass spectral and HNMR analyses. filtered The filtercake is dissolved in CH2Cl2 dried over MgSO4 concentrated in vacuo

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 2-(phenylsulfonylmethyl)-1-nitrobenzene (5.55 g, 20.0 mmol) and granular tin (10.4 g, 88 mmol) in methanol and concentrated HCl (60 mL) is stirred under nitrogen at 45° C. for 5 h, cooled to ambient temperature over an 18 h period, poured onto NaHCO3 (80 g) with stirring, treated with water and extracted with ethyl acetate. The combined extracts are washed with brine (2×100 mL), dried over MgSO4, and concentrated in vacuo to afford the title product as an off-white solid, 4.41 g (89%) mp 175-176° C., identified by HNMR and mass spectral analyses. cooled to ambient temperature over an 18 h period poured onto NaHCO3 (80 g) with stirring extracted with ethyl acetate The combined extracts are washed with brine (2×100 mL) dried over MgSO4 concentrated in vacuo

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

Procedure: A stirred solution of 2-[(phenylsulfonyl)methyl]aniline (247 mg, 1.00 mmol) in 4N HCl (50 ml) is treated with a solution of NaNO2 (100 mg, 1.5 mmol) in water at ice-bath temperatures, stirred for 30 min., neutralized with 10% NaOH and filtered. The filtercake is dissolved in CH2Cl2, dried over MgSO4 and concentrated in vacuo to afford the title product as a tan solid, 240 mg (93% yield), mp 118° C., identified by mass spectral and HNMR analyses. filtered The filtercake is dissolved in CH2Cl2 dried over MgSO4 concentrated in vacuo

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 2-(phenylsulfonylmethyl)-1-nitrobenzene (5.55 g, 20.0 mmol) and granular tin (10.4 g, 88 mmol) in methanol and concentrated HCl (60 mL) is stirred under nitrogen at 45° C. for 5 h, cooled to ambient temperature over an 18 h period, poured onto NaHCO3 (80 g) with stirring, treated with water and extracted with ethyl acetate. The combined extracts are washed with brine (2×100 mL), dried over MgSO4, and concentrated in vacuo to afford the title product as an off-white solid, 4.41 g (89%) mp 175–176° C., identified by HNMR and mass spectral analyses. cooled to ambient temperature over an 18 h period poured onto NaHCO3 (80 g) with stirring extracted with ethyl acetate The combined extracts are washed with brine (2×100 mL) dried over MgSO4 concentrated in vacuo

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

Procedure: A stirred solution of 2-[(phenylsulfonyl)methyl]aniline (247 mg, 1.00 mmol) in 4N HCl (50 ml) is treated with a solution of NaNO2 (100 mg, 1.5 mmol) in water at ice-bath temperatures, stirred for 30 min., neutralized with 10% NaOH and filtered. The filtercake is dissolved in CH2Cl2, dried over MgSO4 and concentrated in vacuo to afford the title product as a tan solid, 240 mg (93% yield), mp 118° C., identified by mass spectral and HNMR analyses. filtered The filtercake is dissolved in CH2Cl2 dried over MgSO4 concentrated in vacuo

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred mixture of 2-(phenylsulfonylmethyl)-1-nitrobenzene (5.55 g, 20.0 mmol) and granular tin (10.4 g, 88 mmol) in methanol and concentrated HCl (60 mL) is stirred under nitrogen at 45° C. for 5 h, cooled to ambient temperature over an 18 h period, poured onto NaHCO3 (80 g) with stirring, treated with water and extracted with ethyl acetate. The combined extracts are washed with brine (2×100 mL), dried over MgSO4, and concentrated in vacuo to afford the title product as an off-white solid, 4.41 g (89%) mp 175-176° C., identified by HNMR and mass spectral analyses. cooled to ambient temperature over an 18 h period poured onto NaHCO3 (80 g) with stirring extracted with ethyl acetate The combined extracts are washed with brine (2×100 mL) dried over MgSO4 concentrated in vacuo