2-phenylsulfanylaniline

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

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

Procedure: Procedure as described for Amidine I using the following amounts and modifications: 10.06 g of 2-phenylthioaniline (50.0 mmol); 25.0 mL of 2.0 M butyllithium (50.0 mmol), 5.20 mL of benzonitrile (51.0 mmol). After refluxing overnight, the solution was green-brown. Addition of water yielded a light brown solution with suspended solid. Solution was taken to dryness, resuspended in 75 mL of pentane, filtered, washed with 10 mL of pentane and dried in vacuo yielding 10.56 g (69%) of beige powder. NMR (400 MHz, C6D6): 7.76 (d, 2H), 7.42 (d, 2H), 7.31 (d, 1H), 7.1-6.8 (m, 8 H), 6.78(t, 1H), 4.08 (s, 2H). After refluxing overnight yielded a light brown solution filtered washed with 10 mL of pentane dried in vacuo

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

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

Procedure: A room temperature solution of 2-fluoronitrobenzene (1.41 g, 10.0 mmol), thiophenol (1.21 g, 11.0 mmol), and triethylamine (2 mL) in THF (20 mL) was stirred for 16 hours, treated with 3M HCl (10 mL) and tin(II) chloride dihydrate (11.4 g, 50 mmol), stirred for 4 hours, and extracted with ethyl acetate (50 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane to provide the desired product. MS (DCI) m/e 202 (M+H)+. extracted with ethyl acetate (50 mL) The combined extracts were dried (MgSO4) filtered concentrated The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane

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

Procedure: A room temperature solution of 2-fluoronitrobenzene (1.41 g, 10.0 mmol), thiophenol (1.21 g, 11.0 mmol), and triethylamine (2 mL) in THF (20 mL) was stirred for 16 hours, treated with 3M HCl (10 mL) and tin(II) chloride dihydrate (11.4 g, 50 mmol), stirred for 4 hours, and extracted with ethyl acetate (50 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane to provide the desired product. MS (DCI) m/e 202 (M+H)+. extracted with ethyl acetate (50 mL) The combined extracts were dried (MgSO4) filtered concentrated The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane

Conditions: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction was carried out without isolation of intermediates in a one pot synthesis. Toluene (30 ml) and phosgene solution (20% in xylene, 9.1 ml, 17.16 mmol) were charged into a reaction flask. The mixture was cooled to −50° C. A mixture of 2-phenylsulfanylphenylamine (3 g, 14.9 mmol), triethylamine (2.4 ml, 17.1 mmol) and toluene (5 ml) was charged into the reaction flask at −50° C. during 5 min. The mixture was allowed to reach room temperature and it was stirred at room temperature for 1.5 h. Then the reaction mixture was added to another reaction flask at −10-0° C., containing the cooled mixture of 1-[2-(hydroxyethoxy)-ethyl]-piperazine, triethylamine (2.7 ml) and toluene (20 ml). The reaction mixture was stirred at room temperature for 1.5 h. Precipitated triethylamine hydrochloride was filtered off. The resulting toluene solution was washed twice with saturated NaCl-water (10 ml), dried with K2CO3 and evaporated in vacuo. The yield of 4-[2-(2-hydroxyethoxy)-ethyl]-piperazine-carboxylic acid (2-phenylsulfanyl-phenyl)-amide was 4.76 g. The reaction was carried out without isolation of intermediates in a one pot synthesis was charged into the reaction flask at −50° C. during 5 min to reach room temperature Then the reaction mixture was added to another reaction flask at −10-0° C. containing The reaction mixture was stirred at room temperature for 1.5 h Precipitated triethylamine hydrochloride was filtered off The resulting toluene solution was washed twice with saturated NaCl-water (10 ml) dried with K2CO3 evaporated in vacuo

Conditions: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction was carried out without isolation of intermediates in a one pot synthesis. Toluene (30 ml) and phosgene solution (20% in xylene, 9.1 ml, 17.16 mmol) were charged into a reaction flask. The mixture was cooled to −50° C. A mixture of 2-phenylsulfanylphenylamine (3 g, 14.9 mmol), triethylamine (2.4 ml, 17.1 mmol) and toluene (5 ml) was charged into the reaction flask at −50° C. during 5 min. The mixture was allowed to reach room temperature and it was stirred at room temperature for 1.5 h. Then the reaction mixture was added to another reaction flask at −10-0° C., containing the cooled mixture of 1-[2-(hydroxyethoxy)-ethyl]-piperazine, triethylamine (2.7 ml) and toluene (20 ml). The reaction mixture was stirred at room temperature for 1.5 h. Precipitated triethylamine hydrochloride was filtered off. The resulting toluene solution was washed twice with saturated NaCl-water (10 ml), dried with K2CO3 and evaporated in vacuo. The yield of 4-[2-(2-hydroxyethoxy)-ethyl]-piperazine-carboxylic acid (2-phenylsulfanyl-phenyl)-amide was 4.76 g. The reaction was carried out without isolation of intermediates in a one pot synthesis was charged into the reaction flask at −50° C. during 5 min to reach room temperature Then the reaction mixture was added to another reaction flask at −10-0° C. containing The reaction mixture was stirred at room temperature for 1.5 h Precipitated triethylamine hydrochloride was filtered off The resulting toluene solution was washed twice with saturated NaCl-water (10 ml) dried with K2CO3 evaporated in vacuo

Conditions: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The reaction was carried out without isolation of intermediates in a one pot synthesis. Toluene (30 ml) and phosgene solution (20% in xylene, 9.1 ml, 17.16 mmol) were charged into a reaction flask. The mixture was cooled to −50° C. A mixture of 2-phenylsulfanylphenylamine (3 g, 14.9 mmol), triethylamine (2.4 ml, 17.1 mmol) and toluene (5 ml) was charged into the reaction flask at −50° C. during 5 min. The mixture was allowed to reach room temperature and it was stirred at room temperature for 1.5 h. Then the reaction mixture was added to another reaction flask at −10-0° C., containing the cooled mixture of 1-[2-(hydroxyethoxy)-ethyl]-piperazine, triethylamine (2.7 ml) and toluene (20 ml). The reaction mixture was stirred at room temperature for 1.5 h. Precipitated triethylamine hydrochloride was filtered off. The resulting toluene solution was washed twice with saturated NaCl-water (10 ml), dried with K2CO3 and evaporated in vacuo. The yield of 4-[2-(2-hydroxyethoxy)-ethyl]-piperazine-carboxylic acid (2-phenylsulfanyl-phenyl)-amide was 4.76 g. The reaction was carried out without isolation of intermediates in a one pot synthesis was charged into the reaction flask at −50° C. during 5 min to reach room temperature Then the reaction mixture was added to another reaction flask at −10-0° C. containing The reaction mixture was stirred at room temperature for 1.5 h Precipitated triethylamine hydrochloride was filtered off The resulting toluene solution was washed twice with saturated NaCl-water (10 ml) dried with K2CO3 evaporated in vacuo

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

Procedure: A room temperature solution of 2-fluoronitrobenzene (1.41 g, 10.0 mmol), thiophenol (1.21 g, 11.0 mmol), and triethylamine (2 mL) in THF (20 mL) was stirred for 16 hours, treated with 3M HCl (10 mL) and tin(II) chloride dihydrate (11.4 g, 50 mmol), stirred for 4 hour, and extracted with ethyl acetate (50 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane to provide the desired product. MS (DCI) m/e 202 (M+H)+. extracted with ethyl acetate (50 mL) The combined extracts were dried (MgSO4) filtered concentrated The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane

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

Procedure: A room temperature solution of 2-fluoronitrobenzene (1.41 g, 10.0 mmol), thiophenol (1.21 g, 11.0 mmol), and triethylamine (2 mL) in THF (20 mL) was stirred for 16 hours, treated with 3M HCl (10 mL) and tin(II) chloride dihydrate (11.4 g, 50 mmol), stirred for 4 hours, and extracted with ethyl acetate (50 mL). The combined extracts were dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane to provide the desired product. MS (DCI) m/e 202 (M+H)+. extracted with ethyl acetate (50 mL) The combined extracts were dried (MgSO4) filtered concentrated The concentrate was purified by flash column chromatography on silica gel with 50% hexanes/dichloromethane

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Amino diphenylsulfide (0.4 mole) was dissolved in toluene (500 ml) and cooled to 5° C. Phenyl chloroformate (0.24 mole) in toluene (50 ml) was added slowly to the stirred solution over 1 hour. When addition was complete a simultaneous addition of phenyl chloroformate (0.24 mole) in toluene (50 ml) and an aqueous solution of sodium hydroxide (0.3 mole) and sodium carbonate (0.35 mole) (200 ml) was started. When addition

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

Procedure: Procedure as described for Amidine I using the following amounts and modifications: 10.06 g of 2-phenylthioaniline (50.0 mmol); 25.0 mL of 2.0 M butyllithium (50.0 mmol), 5.20 mL of benzonitrile (51.0 mmol). After refluxing overnight, the solution was green-brown. Addition of water yielded a light brown solution with suspended solid. Solution was taken to dryness, resuspended in 75 mL of pentane, filtered, washed with 10 mL of pentane and dried in vacuo yielding 10.56 g (69%) of beige powder. NMR (400 MHz, C6D6): 7.76 (d, 2H), 7.42 (d, 2H), 7.31 (d, 1H), 7.1-6.8 (m, 8 H), 6.78(t, 1H), 4.08 (s, 2H). After refluxing overnight yielded a light brown solution filtered washed with 10 mL of pentane dried in vacuo