2-propan-2-ylsulfanylaniline

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

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 34.7 g of 2-chloro-6-nitrophenyl-isopropylsulfane, 140.0 g of methanol and 1 g of Raney nickel 55, as the catalyst (water-moist), were initially introduced into a 0.3 l steel autoclave. After the air had been displaced with nitrogen and hydrogen, hydrogen was forced in at room temperature up to a pressure of 80 bar, while stirring the mixture, a slight increase in temperature already being observed. The mixture was heated to 60° C., while continuing to stir and keep the hydrogen pressure constant. After about 2 hours, the uptake of hydrogen had ended. The mixture was then cooled to room temperature, the hydrogen was let down, the catalyst was filtered off with suction and washed with methanol and the combined filtrates were concentrated. Crude yield: 29.6 g of 2-amino-6-chlorophenyl-isopropylsulfane with a purity of 99.5% (GC), corresponding to 97.5% of theory. The content of 2-isopropylmercaptoaniline formed by hydrogenating dehalogenation was only 0.1%. Furthermore, only 0.1% of impurities due to 3-chloroaniline, formed by hydrogenating desulfurization, were found. was forced in at room temperature up to a pressure of 80 bar a slight increase in temperature to stir The mixture was then cooled to room temperature the catalyst was filtered off with suction washed with methanol the combined filtrates were concentrated

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

Procedure: To a solution of 2-aminothiophenol (90%, 100 g, 0.72 mol) and sodium hydroxide (31.7 g, 0.792 mol) in 90% aqueous ethanol (500 ml) was added dropwise 2-bromopropane (89 g, 0.72 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 3 hours, cooled to room temperature, and then concentrated in vacuo. The residue was diluted with water (300 ml) and extracted with ether (3×500 ml). The ether extracts were washed with water and brine, dried with MgSO4 and concentrated in vacuo to yield the crude product. Distillation through a Vigreaux column gave 2-(1-methylethylthio)benzenamine: bp 94° (2.2-2.4 mm). When the addition the reaction mixture was refluxed for 3 hours concentrated in vacuo The residue was diluted with water (300 ml) extracted with ether (3×500 ml) The ether extracts were washed with water and brine dried with MgSO4 concentrated in vacuo to yield the crude product Distillation through a Vigreaux column

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

Procedure: To a solution of 2-aminothiophenol (90%, 100 g, 0.72 mol) and sodium hydroxide (31.7 g, 0.792 mol) in 90% aqueous ethanol (500 ml) was added dropwise 2-bromopropane (89 g, 0.72 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 3 hours, cooled to room temperature, and then concentrated in vacuo. The residue was diluted with water (300 ml) and extracted with ether (3×500 ml). The ether extracts were washed with water and brine, dried with MgSO4 and concentrated in vacuo to yield the crude product. Distillation through a Vigreaux column gave 2-(1-methylethylthio)benzenamine: bp 94° (2.2-2.4 mm). When the addition the reaction mixture was refluxed for 3 hours concentrated in vacuo The residue was diluted with water (300 ml) extracted with ether (3×500 ml) The ether extracts were washed with water and brine dried with MgSO4 concentrated in vacuo to yield the crude product Distillation through a Vigreaux column

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 34.7 g of 2-chloro-6-nitrophenyl-isopropylsulfane, 140.0 g of methanol and 1 g of Raney nickel 55, as the catalyst (water-moist), were initially introduced into a 0.3 l steel autoclave. After the air had been displaced with nitrogen and hydrogen, hydrogen was forced in at room temperature up to a pressure of 80 bar, while stirring the mixture, a slight increase in temperature already being observed. The mixture was heated to 60° C., while continuing to stir and keep the hydrogen pressure constant. After about 2 hours, the uptake of hydrogen had ended. The mixture was then cooled to room temperature, the hydrogen was let down, the catalyst was filtered off with suction and washed with methanol and the combined filtrates were concentrated. Crude yield: 29.6 g of 2-amino-6-chlorophenyl-isopropylsulfane with a purity of 99.5% (GC), corresponding to 97.5% of theory. The content of 2-isopropylmercaptoaniline formed by hydrogenating dehalogenation was only 0.1%. Furthermore, only 0.1% of impurities due to 3-chloroaniline, formed by hydrogenating desulfurization, were found. was forced in at room temperature up to a pressure of 80 bar a slight increase in temperature to stir The mixture was then cooled to room temperature the catalyst was filtered off with suction washed with methanol the combined filtrates were concentrated

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: A solution of 5,7-dichloro-3-(4-methoxybenzyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (0.03 g) and 2-(isopropylthio)aniline (0.1 g) in dioxane (10 mL) was heated at 100° C. for 10 h. It was then cooled down to room temperature and ethyl acetate (20 mL) was added. The mixture was washed with saturated sodium bicarbonate (10 mL), and dried over sodium sulfate. Solvent was removed under reduced pressure and the remaining residue was purified on a silica gel column (ethyl acetate:hexane=1:10) to give desired product. ESMS calculated for C21H21ClN6OS (m/z): 440.1; found (M+H+): 441.1. The mixture was washed with saturated sodium bicarbonate (10 mL) dried over sodium sulfate Solvent was removed under reduced pressure the remaining residue was purified on a silica gel column (ethyl acetate:hexane=1:10)

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

Procedure: A mixture of 4-chloro-3-methyl-6-methylmercaptopyrazolo[3,4-d]pyrimidine (A-3) (1.21 g, 5.63 mmol) and 2-(isopropylthio)aniline (A-4) (1.42 g, 8.50 mmol) in isopropanol (56 mL) was stirred at reflux for 3 h. After cooling down to ambient temperature, TEA (0.78 mL, 5.66 mmol) was added to the mixture, and the solution was again heated to reflux for 0.5 h. After cooling down to ambient temperature, the mixture was filtered to give the title compound (A-5) as white solid (1.30 g, 3.77 mmol). MS-ESI (m/z): 346 (M+H)+. at reflux for 3 h the solution was again heated to reflux for 0.5 h After cooling down to ambient temperature the mixture was filtered

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

Procedure: To a solution of 2-aminothiophenol (90%, 100 g, 0.72 mol) and sodium hydroxide (31.7 g, 0.792 mol) in 90% aqueous ethanol (500 ml) was added dropwise 2-bromopropane (89 g, 0.72 mol) at room temperature. When the addition was complete, the reaction mixture was refluxed for 3 hours, cooled to room temperature, and then concentrated in vacuo. The residue was diluted with water (300 ml) and extracted with ether (3×500 ml). The ether extracts were washed with water and brine, dried with MgSO4 and concentrated in vacuo to yield the crude product. Distillation through a Vigreaux column gave 2-(1-methylethylthio)benzenamine: bp 94° (2.2-2.4 mm). When the addition the reaction mixture was refluxed for 3 hours concentrated in vacuo The residue was diluted with water (300 ml) extracted with ether (3×500 ml) The ether extracts were washed with water and brine dried with MgSO4 concentrated in vacuo to yield the crude product Distillation through a Vigreaux column

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 34.7 g of 2-chloro-6-nitrophenyl-isopropylsulfane, 140.0 g of methanol and 1 g of Raney nickel 55, as the catalyst (water-moist), were initially introduced into a 0.3 l steel autoclave. After the air had been displaced with nitrogen and hydrogen, hydrogen was forced in at room temperature up to a pressure of 80 bar, while stirring the mixture, a slight increase in temperature already being observed. The mixture was heated to 60° C., while continuing to stir and keep the hydrogen pressure constant. After about 2 hours, the uptake of hydrogen had ended. The mixture was then cooled to room temperature, the hydrogen was let down, the catalyst was filtered off with suction and washed with methanol and the combined filtrates were concentrated. Crude yield: 29.6 g of 2-amino-6-chlorophenyl-isopropylsulfane with a purity of 99.5% (GC), corresponding to 97.5% of theory. The content of 2-isopropylmercaptoaniline formed by hydrogenating dehalogenation was only 0.1%. Furthermore, only 0.1% of impurities due to 3-chloroaniline, formed by hydrogenating desulfurization, were found. was forced in at room temperature up to a pressure of 80 bar a slight increase in temperature to stir The mixture was then cooled to room temperature the catalyst was filtered off with suction washed with methanol the combined filtrates were concentrated