4-ethylsulfonylaniline

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

Procedure: (1-Methylethyl)sulfamoyl chloride (6.63 g, 0.034 mol) was added dropwise to a solution of 4-(ethylsulfonyl)benzene amine (6 g, 0.032 mol) and triethylamine (4.87 ml, 0.035 mol) in dry dichloromethane (100 ml) at 0° C. under a nitrogen atmosphere. After addition, the resultant mixture was allowed to warm to room temperature and was stirred for 6 hr. The reaction mixture was then washed with water (2×50 ml). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to yield N-(4-ethylsulfonylphenyl)-N′-(1-methylethyl)sulfamide as a white solid. δ(1H NMR, DMSO, ppm): 1.05 (6H, d), 1.10 (3H, t), 3.25 (2H, q), 3.40 (1H, m), 7.40 (2H, d), 7.80 (3H, m). After addition The reaction mixture was then washed with water (2×50 ml) dried (MgSO4) concentrated in vacuo

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

Procedure: (1-Methylethyl)sulfamoyl chloride (6.63 g, 0.034 mol) was added dropwise to a solution of 4-(ethylsulfonyl)benzene amine (6 g, 0.032 mol) and triethylamine (4.87 ml, 0.035 mol) in dry dichloromethane (100 ml) at 0° C. under a nitrogen atmosphere. After addition, the resultant mixture was allowed to warm to room temperature and was stirred for 6 hr. The reaction mixture was then washed with water (2×50 ml). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to yield N-(4-ethylsulfonylphenyl)-N′-(1-methylethyl)sulfamide as a white solid. δ(1H NMR, DMSO, ppm): 1.05 (6H, d), 1.10 (3H, t), 3.25 (2H, q), 3.40 (1H, m), 7.40 (2H, d), 7.80 (3H, m). After addition The reaction mixture was then washed with water (2×50 ml) dried (MgSO4) concentrated in vacuo

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

Procedure: (1-Methylethyl)sulfamoyl chloride (6.63 g, 0.034 mol) was added dropwise to a solution of 4-(ethylsulfonyl)benzene amine (6 g, 0.032 mol) and triethylamine (4.87 ml, 0.035 mol) in dry dichloromethane (100 ml) at 0° C. under a nitrogen atmosphere. After addition, the resultant mixture was allowed to warm to room temperature and was stirred for 6 hr. The reaction mixture was then washed with water (2×50 ml). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to yield N-(4-ethylsulfonylphenyl)-N′-(1-methylethyl)sulfamide as a white solid. δ(1H NMR, DMSO, ppm): 1.05 (6H, d), 1.10 (3H, t), 3.25 (2H, q), 3.40 (1H, m), 7.40 (2H, d), 7.80 (3H, m). After addition The reaction mixture was then washed with water (2×50 ml) dried (MgSO4) concentrated in vacuo

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

Procedure: Tin (II) chloride dihydrate (51.89 g, 0.230 mol) was added to 1-(ethylsulfonyl)-4-nitrobenzene (10 g, 0.046 mol) in ethanol (250 ml) then heated under reflux for 16 h. The mixture was cooled to room temperature and treated with aqueous sodium hydroxide (2N, 100 ml). The product was then extracted into ethyl acetate (3×150 ml). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo. The residue was then purified by chromatography column over silica (50% ethyl acetate/50% petroleum ether) to afford 4-(ethylsulfonyl)-benzene amine. δ(1H NMR, DMSO, ppm): 1.00 (3H, t), 2.95 (2H, q), 5.95 (2H, s), 6.55 (2H, d), 7.35(2H, d). then heated under reflux for 16 h The product was then extracted into ethyl acetate (3×150 ml) dried (MgSO4) concentrated in vacuo The residue was then purified by chromatography column over silica (50% ethyl acetate/50% petroleum ether)

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

Procedure: Tin (II) chloride dihydrate (51.89 g, 0.230 mol) was added to 1-(ethylsulfonyl)-4-nitrobenzene (10 g, 0.046 mol) in ethanol (250 ml) then heated under reflux for 16 h. The mixture was cooled to room temperature and treated with aqueous sodium hydroxide (2N, 100 ml). The product was then extracted into ethyl acetate (3×150 ml). The organic extracts were combined, dried (MgSO4) and concentrated in vacuo. The residue was then purified by chromatography column over silica (50% ethyl acetate/50% petroleum ether) to afford 4-(ethylsulfonyl)-benzene amine. δ(1H NMR, DMSO, ppm): 1.00 (3H, t), 2.95 (2H, q), 5.95 (2H, s), 6.55 (2H, d), 7.35(2H, d). then heated under reflux for 16 h The product was then extracted into ethyl acetate (3×150 ml) dried (MgSO4) concentrated in vacuo The residue was then purified by chromatography column over silica (50% ethyl acetate/50% petroleum ether)