ethyl N-[(4-aminophenyl)-methyl-oxo-lambda6-sulfanylidene]carbamate

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

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

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

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

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

Procedure: (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide (10 g, 42 mmol), 5-bromo-2-chloro-4-methylsulfanyl-pyrimidine (10 g, 42 mmol) and 5M HCl (8 mL) in dioxane is stirred at 60° C. in 90% acetonitrile-water (250 mL) for 36 h. TLC indicates almost complete consumption of starting sulfoximine. The reaction mixture is poured into 800 mL of aq. NaHCO3, the pasty precipitate filtered, washed with 70 mL of EtOAc, then crude material (7.5 g) is recrystallized from boiling EtOH (200 mL) to yield 6 g (35%). consumption of starting sulfoximine The reaction mixture is poured into 800 mL of aq. NaHCO3 the pasty precipitate filtered washed with 70 mL of EtOAc crude material (7.5 g) is recrystallized to yield 6 g (35%)

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

Procedure: A solution of 8.70 g (32.0 mmol) (RS)—N-(ethoxycarbonyl)-S-methyl-S-(4-nitro-phenyl)sulfoximide in 650 ml THF is slowly treated at room temperature with 435 ml of a 10% solution of Ti(III)Cl3 in approximately 10% hydrochloric acid (Aldrich). The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. 450 ml of a 32% NaOH solution are added dropwise. During this, the reaction mixture is periodically diluted by the addition of water and ethyl acetate. It is treated with 500 ml ethyl acetate and the organic phase is separated. The mushy aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with dilute NaCl solution, dried (Na2SO4), filtered and concentrated. 8.05 g (ca. 32.0 mmol) of the product is obtained, which is used without further purification. cooled to 0° C the organic phase is separated The mushy aqueous phase is extracted with ethyl acetate The combined organic phases are washed with dilute NaCl solution dried (Na2SO4) filtered concentrated

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

Procedure: (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide (10 g, 42 mmol), 5-bromo-2-chloro-4-methylsulfanyl-pyrimidine (10 g, 42 mmol) and 5M HCl (8 mL) in dioxane is stirred at 60° C. in 90% acetonitrile-water (250 mL) for 36 h. TLC indicates almost complete consumption of starting sulfoximine. The reaction mixture is poured into 800 mL of aq. NaHCO3, the pasty precipitate filtered, washed with 70 mL of EtOAc, then crude material (7.5 g) is recrystallized from boiling EtOH (200 mL) to yield 6 g (35%). consumption of starting sulfoximine The reaction mixture is poured into 800 mL of aq. NaHCO3 the pasty precipitate filtered washed with 70 mL of EtOAc crude material (7.5 g) is recrystallized to yield 6 g (35%)

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

Procedure: A solution of 8.70 g (32.0 mmol) (RS)—N-(ethoxycarbonyl)-S-methyl-S-(4-nitro-phenyl)sulfoximide in 650 ml THF is slowly treated at room temperature with 435 ml of a 10% solution of Ti(III)Cl3 in approximately 10% hydrochloric acid (Aldrich). The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. 450 ml of a 32% NaOH solution are added dropwise. During this, the reaction mixture is periodically diluted by the addition of water and ethyl acetate. It is treated with 500 ml ethyl acetate and the organic phase is separated. The mushy aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with dilute NaCl solution, dried (Na2SO4), filtered and concentrated. 8.05 g (ca. 32.0 mmol) of the product is obtained, which is used without further purification. cooled to 0° C the organic phase is separated The mushy aqueous phase is extracted with ethyl acetate The combined organic phases are washed with dilute NaCl solution dried (Na2SO4) filtered concentrated

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

Procedure: (RS)—S-(4-aminophenyl)-N-(ethoxycarbonyl)-S-methylsulfoximide (10 g, 42 mmol), 5-bromo-2-chloro-4-methylsulfanyl-pyrimidine (10 g, 42 mmol) and 5M HCl (8 mL) in dioxane is stirred at 60° C. in 90% acetonitrile-water (250 mL) for 36 h. TLC indicates almost complete consumption of starting sulfoximine. The reaction mixture is poured into 800 mL of aq. NaHCO3, the pasty precipitate filtered, washed with 70 mL of EtOAc, then crude material (7.5 g) is recrystallized from boiling EtOH (200 mL) to yield 6 g (35%). consumption of starting sulfoximine The reaction mixture is poured into 800 mL of aq. NaHCO3 the pasty precipitate filtered washed with 70 mL of EtOAc crude material (7.5 g) is recrystallized to yield 6 g (35%)

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

Procedure: A solution of 8.70 g (32.0 mmol) (RS)—N-(ethoxycarbonyl)-S-methyl-S-(4-nitro-phenyl)sulfoximide in 650 ml THF is slowly treated at room temperature with 435 ml of a 10% solution of Ti(III)Cl3 in approximately 10% hydrochloric acid (Aldrich). The mixture is stirred at room temperature for 4 hours and then cooled to 0° C. 450 ml of a 32% NaOH solution are added dropwise. During this, the reaction mixture is periodically diluted by the addition of water and ethyl acetate. It is treated with 500 ml ethyl acetate and the organic phase is separated. The mushy aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with dilute NaCl solution, dried (Na2SO4), filtered and concentrated. 8.05 g (ca. 32.0 mmol) of the product is obtained, which is used without further purification. cooled to 0° C the organic phase is separated The mushy aqueous phase is extracted with ethyl acetate The combined organic phases are washed with dilute NaCl solution dried (Na2SO4) filtered concentrated

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

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