(4-bromophenyl)-imino-methyl-oxo-lambda6-sulfane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedures given for the Mannich reaction in Canadian Patent 1,102,803, the title compound is prepared from S-(4-bromophenyl)-S-methylsulfoximine, pyrrolidine, and 37% formaldehyde solution. given for the Mannich reaction in Canadian Patent 1,102,803

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedures given for the Mannich reaction in Canadian Patent 1,102,803, the title compound is prepared from S-(4-bromophenyl)-S-methylsulfoximine, pyrrolidine, and 37% formaldehyde solution. given for the Mannich reaction in Canadian Patent 1,102,803

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromophenyl-methylsulfoximine (10.0 g, 42.7 mmol) in dimethylformamide (50 mL) was added dropwise to a stirring slurry of sodium hydride (2.04 g, 51.2 mmol, 60% oil dispersion washed (3×20 mL) with hexane) which was maintained at 0° C. After stirring for 30 minutes, a solution of diethylaminoethyl chloride (6.58 g, 48.3 mmol) in dimethylformamide (20 mL) was added dropwise. The reaction mixture was warmed at 60° C. for 18 h. The reaction mixture was then cooled to ambient temperature, and 5 mL of water was added. The resulting solution was concentrated in vacuo. The residue was partitioned between 0.1N aqueous HCl (100 mL) and methylene chloride (100 mL). The layers were separated, and the aqueous layer was extracted with methylene chloride (2×50 mL). The aqueous layer was then made basic with 50% aqueous sodium hydroxide, and the resulting slurry was extracted with methylene chloride. These combined organic extracts were washed with saturated sodium chloride, dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed (flash, SiO2, 9:1 methylene chloride:methanol) to give 9.1 g (62%) of clear oil. The reaction mixture was warmed at 60° C. for 18 h The reaction mixture was then cooled to ambient temperature The resulting solution was concentrated in vacuo The residue was partitioned between 0.1N aqueous HCl (100 mL) and methylene chloride (100 mL) The layers were separated the aqueous layer was extracted with methylene chloride (2×50 mL) the resulting slurry was extracted with methylene chloride These combined organic extracts were washed with saturated sodium chloride dried (Na2SO4) concentrated in vacuo The residue was chromatographed (flash, SiO2, 9:1 methylene chloride:methanol)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromophenyl-methylsulfoximine (10.0 g, 42.7 mmol) in dimethylformamide (50 mL) was added dropwise to a stirring slurry of sodium hydride (2.04 g, 51.2 mmol, 60% oil dispersion washed (3×20 mL) with hexane) which was maintained at 0° C. After stirring for 30 minutes, a solution of diethylaminoethyl chloride (6.58 g, 48.3 mmol) in dimethylformamide (20 mL) was added dropwise. The reaction mixture was warmed at 60° C. for 18 h. The reaction mixture was then cooled to ambient temperature, and 5 mL of water was added. The resulting solution was concentrated in vacuo. The residue was partitioned between 0.1N aqueous HCl (100 mL) and methylene chloride (100 mL). The layers were separated, and the aqueous layer was extracted with methylene chloride (2×50 mL). The aqueous layer was then made basic with 50% aqueous sodium hydroxide, and the resulting slurry was extracted with methylene chloride. These combined organic extracts were washed with saturated sodium chloride, dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed (flash, SiO2, 9:1 methylene chloride:methanol) to give 9.1 g (62%) of clear oil. The reaction mixture was warmed at 60° C. for 18 h The reaction mixture was then cooled to ambient temperature The resulting solution was concentrated in vacuo The residue was partitioned between 0.1N aqueous HCl (100 mL) and methylene chloride (100 mL) The layers were separated the aqueous layer was extracted with methylene chloride (2×50 mL) the resulting slurry was extracted with methylene chloride These combined organic extracts were washed with saturated sodium chloride dried (Na2SO4) concentrated in vacuo The residue was chromatographed (flash, SiO2, 9:1 methylene chloride:methanol)

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Following the procedures given for the Mannich reaction in Canadian Patent 1,102,803, the title compound is prepared from S-(4-bromophenyl)-S-methylsulfoximine, pyrrolidine, and 37% formaldehyde solution. given for the Mannich reaction in Canadian Patent 1,102,803

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 4-bromophenyl-methylsulfoximine (10.0 g, 42.7 mmol) in dimethylformamide (50 mL) was added dropwise to a stirring slurry of sodium hydride (2.04 g, 51.2 mmol, 60% oil dispersion washed (3×20 mL) with hexane) which was maintained at 0° C. After stirring for 30 minutes, a solution of diethylaminoethyl chloride (6.58 g, 48.3 mmol) in dimethylformamide (20 mL) was added dropwise. The reaction mixture was warmed at 60° C. for 18 h. The reaction mixture was then cooled to ambient temperature, and 5 mL of water was added. The resulting solution was concentrated in vacuo. The residue was partitioned between 0.1N aqueous HCl (100 mL) and methylene chloride (100 mL). The layers were separated, and the aqueous layer was extracted with methylene chloride (2×50 mL). The aqueous layer was then made basic with 50% aqueous sodium hydroxide, and the resulting slurry was extracted with methylene chloride. These combined organic extracts were washed with saturated sodium chloride, dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed (flash, SiO2, 9:1 methylene chloride:methanol) to give 9.1 g (62%) of clear oil. The reaction mixture was warmed at 60° C. for 18 h The reaction mixture was then cooled to ambient temperature The resulting solution was concentrated in vacuo The residue was partitioned between 0.1N aqueous HCl (100 mL) and methylene chloride (100 mL) The layers were separated the aqueous layer was extracted with methylene chloride (2×50 mL) the resulting slurry was extracted with methylene chloride These combined organic extracts were washed with saturated sodium chloride dried (Na2SO4) concentrated in vacuo The residue was chromatographed (flash, SiO2, 9:1 methylene chloride:methanol)

反応条件: temp:0.00; pressure:0.00; stir: