4-苯甲酰基苯磺酰胺

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thionyl chloride (25 mL, 0.34 mol) was added dropwise to ethanol (540 mL). The reaction was heated to reflux for 15 minutes and cooled. The solution was treated with 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one from Step 1 (20.0 g, 72.64 mmol) and acetonylacetone (12.8 mL, 108.96 mmol), and reheated to reflux for 30 minutes. After cooling to room temperature, the solution was poured into rapidly stirred saturated aqueous Na2CO3 and ice (1500 mL). The aqueous phase was extracted with ethyl acetate (2×700 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo, yielding a brown oil. The oil was diluted with ethyl acetate (200 mL) and hexane (2000 mL), dried with MgSO4, gravity filtered, then purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant. The material was concentrated in vacuo and crystallized from hexane/ethyl acetate. The solid was isolated by filtration and air dried to afford 2,5-dimethyl-1-[[4-(2-oxo-2-phenylethyl)phenyl]sulfonyl]-1H-pyrrole (12.2 g, 49%) as a brown solid: mp 94.6°-98.8° C. 1H NMR (DMSO-d6 /300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 1H), 7.44 (d, J=8.26 Hz, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). Mass spectrum: M+H obs. at m/z=354. The reaction was heated to reflux for 15 minutes cooled to reflux for 30 minutes The aqueous phase was extracted with ethyl acetate (2×700 mL) The combined organics were washed with brine dried over MgSO4 filtered concentrated in vacuo yielding a brown oil dried with MgSO4, gravity filtered purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant The material was concentrated in vacuo crystallized from hexane/ethyl acetate The solid was isolated by filtration and air dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Chlorosulfonic acid (1781 g, 1018 mL, 15.29 mol) was treated portionwise with deoxybenzoin (400 g, 2.04 mol) at such a rate that the internal temperature was maintained between 5° and 15° C. The mixture was warmed to room temperature and maintained at that temperature for an additional 14 hours. The mixture was poured cautiously into ice water. The crude sulfonyl chloride was filtered and added portionwise to a solution of acetone (600 mL) and concentrated NH4OH (551 mL, 8.15 mol), yielding a pale yellow suspension. The crude precipitate was collected by vacuum filtration, and triturated with boiling acetone (1.5 L). Filtration afforded 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one (162 g, 29%) as an off-white powder: 1H NMR (DMSO-d6, 300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 2H), 7.44 (d, J=8.26, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). was maintained between 5° and 15° C maintained at that temperature for an additional 14 hours The crude sulfonyl chloride was filtered yielding a pale yellow suspension The crude precipitate was collected by vacuum filtration triturated with boiling acetone (1.5 L) Filtration

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 14.4 g (52 mmol) of 2-(4-aminosulfonylphenyl)-1-phenylethanone in 240 mL of glacial acetic acid stirred under nitrogen, a solution of 24 mL of hydrobromic acid in glacial acetic acid (33%) was added. To the reaction mixture was added slowly 8.4 g (52 mmol) of bromine. It was stirred at room temperature until complete loss of the colour. After concentration, the resulting residue was dissolved in ethyl acetate (500 mL). The organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL). The organic layer was dried, filtered and concentrated in vacuum. The residue was swished in hexane to give 14.9 g (80%) of the desired solid as a white powdered solid. It was stirred at room temperature until complete loss of the colour After concentration the resulting residue was dissolved in ethyl acetate (500 mL) The organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL) The organic layer was dried filtered concentrated in vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 14.4 g (52 mmol) of 2-(4-aminosulfonylphenyl)-1-phenylethanone in 240 mL of glacial acetic acid stirred under nitrogen, a solution of 24 mL of hydrobromic acid in glacial acetic acid (33%) was added. To the reaction mixture was added slowly 8.4 g (52 mmol) of bromine. It was stirred at room temperature until complete loss of the colour. After concentration, the resulting residue was dissolved in ethyl acetate (500 mL). The organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL). The organic layer was dried, filtered and concentrated in vacuum. The residue was swished in hexane to give 14.9 g (80%) of the desired solid as a white powdered solid. It was stirred at room temperature until complete loss of the colour After concentration the resulting residue was dissolved in ethyl acetate (500 mL) The organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL) The organic layer was dried filtered concentrated in vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thionyl chloride (25 mL, 0.34 mol) was added dropwise to ethanol (540 mL). The reaction was heated to reflux for 15 minutes and cooled. The solution was treated with 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one from Step 1 (20.0 g, 72.64 mmol) and acetonylacetone (12.8 mL, 108.96 mmol), and reheated to reflux for 30 minutes. After cooling to room temperature, the solution was poured into rapidly stirred saturated aqueous Na2CO3 and ice (1500 mL). The aqueous phase was extracted with ethyl acetate (2×700 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo, yielding a brown oil. The oil was diluted with ethyl acetate (200 mL) and hexane (2000 mL), dried with MgSO4, gravity filtered, then purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant. The material was concentrated in vacuo and crystallized from hexane/ethyl acetate. The solid was isolated by filtration and air dried to afford 2,5-dimethyl-1-[[4-(2-oxo-2-phenylethyl)phenyl]sulfonyl]-1H-pyrrole (12.2 g, 49%) as a brown solid: mp 94.6°-98.8° C. 1H NMR (DMSO-d6 /300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 1H), 7.44 (d, J=8.26 Hz, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). Mass spectrum: M+H obs. at m/z=354. The reaction was heated to reflux for 15 minutes cooled to reflux for 30 minutes The aqueous phase was extracted with ethyl acetate (2×700 mL) The combined organics were washed with brine dried over MgSO4 filtered concentrated in vacuo yielding a brown oil dried with MgSO4, gravity filtered purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant The material was concentrated in vacuo crystallized from hexane/ethyl acetate The solid was isolated by filtration and air dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Chlorosulfonic acid (1781 g, 1018 mL, 15.29 mol) was treated portionwise with deoxybenzoin (400 g, 2.04 mol) at such a rate that the internal temperature was maintained between 5° and 15° C. The mixture was warmed to room temperature and maintained at that temperature for an additional 14 hours. The mixture was poured cautiously into ice water. The crude sulfonyl chloride was filtered and added portionwise to a solution of acetone (600 mL) and concentrated NH4OH (551 mL, 8.15 mol), yielding a pale yellow suspension. The crude precipitate was collected by vacuum filtration, and triturated with boiling acetone (1.5 L). Filtration afforded 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one (162 g, 29%) as an off-white powder: 1H NMR (DMSO-d6, 300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 2H), 7.44 (d, J=8.26, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). was maintained between 5° and 15° C maintained at that temperature for an additional 14 hours The crude sulfonyl chloride was filtered yielding a pale yellow suspension The crude precipitate was collected by vacuum filtration triturated with boiling acetone (1.5 L) Filtration

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thionyl chloride (25 mL, 0.34 mol) was added dropwise to ethanol (540 mL). The reaction was heated to reflux for 15 minutes and cooled. The solution was treated with 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one from Step 1 (20.0 g, 72.64 mmol) and acetonylacetone (12.8 mL, 108.96 mmol), and reheated to reflux for 30 minutes. After cooling to room temperature, the solution was poured into rapidly stirred saturated aqueous Na2CO3 and ice (1500 mL). The aqueous phase was extracted with ethyl acetate (2×700 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo, yielding a brown oil. The oil was diluted with ethyl acetate (200 mL) and hexane (2000 mL), dried with MgSO4, gravity filtered, then purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant. The material was concentrated in vacuo and crystallized from hexane/ethyl acetate. The solid was isolated by filtration and air dried to afford 2,5-dimethyl-1-[[4-(2-oxo-2-phenylethyl)phenyl]sulfonyl]-1H-pyrrole (12.2 g, 49%) as a brown solid: mp 94.6°-98.8° C. 1H NMR (DMSO-d6 /300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 1H), 7.44 (d, J=8.26 Hz, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). Mass spectrum: M+H obs. at m/z=354. The reaction was heated to reflux for 15 minutes cooled to reflux for 30 minutes The aqueous phase was extracted with ethyl acetate (2×700 mL) The combined organics were washed with brine dried over MgSO4 filtered concentrated in vacuo yielding a brown oil dried with MgSO4, gravity filtered purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant The material was concentrated in vacuo crystallized from hexane/ethyl acetate The solid was isolated by filtration and air dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 14.4 g (52 mmol) of 2-(4-aminosulfonylphenyl)-1-phenylethanone in 240 mL of glacial acetic acid stirred under nitrogen, a solution of 24 mL of hydrobromic acid in glacial acetic acid (33%) was added. To the reaction mixture was added slowly 8.4 g (52 mmol) of bromine. It was stirred at room temperature until complete loss of the colour. After concentration, the resulting residue was dissolved in ethyl acetate (500 mL). The organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL). The organic layer was dried, filtered and concentrated in vacuum. The residue was swished in hexane to give 14.9 g (80%) of the desired solid as a white powdered solid. It was stirred at room temperature until complete loss of the colour After concentration the resulting residue was dissolved in ethyl acetate (500 mL) The organic layer was washed twice with 5% aqueous sodium bicarbonate solution (2×350 mL) and with brine (350 mL) The organic layer was dried filtered concentrated in vacuum

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Thionyl chloride (25 mL, 0.34 mol) was added dropwise to ethanol (540 mL). The reaction was heated to reflux for 15 minutes and cooled. The solution was treated with 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one from Step 1 (20.0 g, 72.64 mmol) and acetonylacetone (12.8 mL, 108.96 mmol), and reheated to reflux for 30 minutes. After cooling to room temperature, the solution was poured into rapidly stirred saturated aqueous Na2CO3 and ice (1500 mL). The aqueous phase was extracted with ethyl acetate (2×700 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo, yielding a brown oil. The oil was diluted with ethyl acetate (200 mL) and hexane (2000 mL), dried with MgSO4, gravity filtered, then purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant. The material was concentrated in vacuo and crystallized from hexane/ethyl acetate. The solid was isolated by filtration and air dried to afford 2,5-dimethyl-1-[[4-(2-oxo-2-phenylethyl)phenyl]sulfonyl]-1H-pyrrole (12.2 g, 49%) as a brown solid: mp 94.6°-98.8° C. 1H NMR (DMSO-d6 /300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 1H), 7.44 (d, J=8.26 Hz, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). Mass spectrum: M+H obs. at m/z=354. The reaction was heated to reflux for 15 minutes cooled to reflux for 30 minutes The aqueous phase was extracted with ethyl acetate (2×700 mL) The combined organics were washed with brine dried over MgSO4 filtered concentrated in vacuo yielding a brown oil dried with MgSO4, gravity filtered purified through a short silica gel column with hexane and ethyl acetate (1:1) as eluant The material was concentrated in vacuo crystallized from hexane/ethyl acetate The solid was isolated by filtration and air dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Chlorosulfonic acid (1781 g, 1018 mL, 15.29 mol) was treated portionwise with deoxybenzoin (400 g, 2.04 mol) at such a rate that the internal temperature was maintained between 5° and 15° C. The mixture was warmed to room temperature and maintained at that temperature for an additional 14 hours. The mixture was poured cautiously into ice water. The crude sulfonyl chloride was filtered and added portionwise to a solution of acetone (600 mL) and concentrated NH4OH (551 mL, 8.15 mol), yielding a pale yellow suspension. The crude precipitate was collected by vacuum filtration, and triturated with boiling acetone (1.5 L). Filtration afforded 2-[4-aminosulfonylphenyl]-1-phenyl-ethan-1-one (162 g, 29%) as an off-white powder: 1H NMR (DMSO-d6, 300 MHz) 8.05 (d, J=7.25 Hz, 2H), 7.76 (d, J=8.26 Hz, 2H), 7.65 (t, J=7.85 Hz, 1H), 7.54 (t, J=7.85 Hz, 2H), 7.44 (d, J=8.26, 2H), 7.30 (br s, 2H), 4.52 (s, 2H). was maintained between 5° and 15° C maintained at that temperature for an additional 14 hours The crude sulfonyl chloride was filtered yielding a pale yellow suspension The crude precipitate was collected by vacuum filtration triturated with boiling acetone (1.5 L) Filtration