2-amino-N-propylbenzenesulfonamide

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

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

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2,4-dichloropyrimidine (90 μL, 0.70 mmol) and 2-amino-N-propyl-benzenesulfonamide (100 mg, 0.47 mmol), sodium hydride (54.2 mg, 0.56 mmol) in DMSO (1.0 mL) is added and the resulting solution is stirred at 80° C. for 3.0 h. The mixture is poured into water and extracted with ethyl acetate three times. The organic layer is washed with water and then brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford the title compound as a slightly yellow solid. extracted with ethyl acetate three times The organic layer is washed with water brine, dried over sodium sulfate evaporated in vacuo The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2,4-dichloropyrimidine (90 μL, 0.70 mmol) and 2-amino-N-propyl-benzenesulfonamide (100 mg, 0.47 mmol), sodium hydride (54.2 mg, 0.56 mmol) in DMSO (1.0 mL) is added and the resulting solution is stirred at 80° C. for 3.0 h. The mixture is poured into water and extracted with ethyl acetate three times. The organic layer is washed with water and then brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford the title compound as a slightly yellow solid. extracted with ethyl acetate three times The organic layer is washed with water brine, dried over sodium sulfate evaporated in vacuo The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2,4-dichloropyrimidine (90 μL, 0.70 mmol) and 2-amino-N-propyl-benzenesulfonamide (100 mg, 0.47 mmol), sodium hydride (54.2 mg, 0.56 mmol) in DMSO (1.0 mL) is added and the resulting solution is stirred at 80° C. for 3.0 h. The mixture is poured into water and extracted with ethyl acetate three times. The organic layer is washed with water and then brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford the title compound as a slightly yellow solid. extracted with ethyl acetate three times The organic layer is washed with water brine, dried over sodium sulfate evaporated in vacuo The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2,4-dichloropyrimidine (90 μL, 0.70 mmol) and 2-amino-N-propyl-benzenesulfonamide (100 mg, 0.47 mmol), sodium hydride (54.2 mg, 0.56 mmol) in DMSO (1.0 mL) is added and the resulting solution is stirred at 80° C. for 3.0 h. The mixture is poured into water and extracted with ethyl acetate three times. The organic layer is washed with water and then brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford the title compound as a slightly yellow solid. extracted with ethyl acetate three times The organic layer is washed with water brine, dried over sodium sulfate evaporated in vacuo The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

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

Procedure: To a solution of 2-nitro-N-propylbenzenesulfonamide (8.64 g, 0.035 mol) in methanol (100 mL) was added palladium on carbon (10%, 3.5 g). The mixture was stirred under an atmosphere of hydrogen for 12 hours. The catalyst was removed by filtration and the filtrate was evaporated. The solid residue was washed with ether to afford 2-amino-N-propylbenzenesulfonamide (7.45 g, yield 98.3%), which was dissolved in ether, and bubbled in hydrochloride (gas) to afford the product 2-amino-N-propylbenzenesulfonamide hydrochloride (8.61 g, yield 98.4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (br s, 3H), 7.50-7.62 (m, 2H), 7.26-7.30 (dt, 1H, J=1.6 Hz, 7.6 Hz), 6.88-6.90 (d, 1H, J=8.0 Hz), 6.67-6.71 (m, 1H), 2.61-2.65 (t, 2H, J=7.2 Hz), 1.28-1.37 (sext, 2H, J=7.2 Hz), 0.72-0.76 (t, 3H, J=7.6 Hz). The catalyst was removed by filtration the filtrate was evaporated The solid residue was washed with ether

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-bromo-2,4-dichloropyrimidine (90 μL, 0.70 mmol) and 2-amino-N-propyl-benzenesulfonamide (100 mg, 0.47 mmol), sodium hydride (54.2 mg, 0.56 mmol) in DMSO (1.0 mL) is added and the resulting solution is stirred at 80° C. for 3.0 h. The mixture is poured into water and extracted with ethyl acetate three times. The organic layer is washed with water and then brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1) to afford the title compound as a slightly yellow solid. extracted with ethyl acetate three times The organic layer is washed with water brine, dried over sodium sulfate evaporated in vacuo The residue is purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)