3-ethylsulfanylaniline

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: To a solution of 3-aminobenzenethiol (5.0 g, 39.9 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (6.62 g, 47.9 mmol) and iodoethane (3.19 mL, 39.9 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (3 times). The combined organic extracts were washed with brine (2 times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes) to afford 3-(ethylthio)aniline (5.12 g, 84% yield). MS (m/z) 154.1 (M+H+). extracted with ethyl acetate (3 times) The combined organic extracts were washed with brine (2 times) dried over Na2SO4 filtered concentrated in vacuo The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes)

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

Procedure: To a solution of 3-aminobenzenethiol (5.0 g, 39.9 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (6.62 g, 47.9 mmol) and iodoethane (3.19 mL, 39.9 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (3 times). The combined organic extracts were washed with brine (2 times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes) to afford 3-(ethylthio)aniline (5.12 g, 84% yield). MS (m/z) 154.1 (M+H+). extracted with ethyl acetate (3 times) The combined organic extracts were washed with brine (2 times) dried over Na2SO4 filtered concentrated in vacuo The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes)

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

Procedure: Sodium hydride (60% in oil, 2.3 g) was suspended in a mixed solvent of tetrahydrofuran (35 mL) and N,N-dimethylformamide (15 mL), and 3-aminobenzenethiol (5.0 g) was added dropwise at room temperature. The mixture was stirred at the same temperature for 5 min, iodoethane (6.86 g) was added, and the mixture was stirred for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a yellow oil (yield 5.0 g, 82%). was added dropwise at room temperature the mixture was stirred for 30 min the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

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

Procedure: To a suspension of 25 grams (0.193 mole; M.W. 125.19) of 3-aminothiophenol in 200 ml. of 5N sodium hydroxide was added, dropwise, over a period of 1 hour, a solution of 29.9 grams (0.193 mole) of ethyl iodide in 50 ml. of 1,4-dioxane. The resulting suspension was allowed to stir at room temperature for 1 hour, 200 ml. of ethyl ether were then added, and stirring was continued for an additional 30 minutes. The ether layer was separated, washed with a saturated aqueous solution of sodium bisulfite, dried over Na2SO4, and evaporated in vacuo to yield 28.10 grams of m-ethylthioaniline. stirring was continued for an additional 30 minutes The ether layer was separated washed with a saturated aqueous solution of sodium bisulfite dried over Na2SO4 evaporated in vacuo

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

Procedure: To a solution of 3-aminobenzenethiol (5.0 g, 39.9 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (6.62 g, 47.9 mmol) and iodoethane (3.19 mL, 39.9 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (3 times). The combined organic extracts were washed with brine (2 times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes) to afford 3-(ethylthio)aniline (5.12 g, 84% yield). MS (m/z) 154.1 (M+H+). extracted with ethyl acetate (3 times) The combined organic extracts were washed with brine (2 times) dried over Na2SO4 filtered concentrated in vacuo The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes)

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

Procedure: Sodium hydride (60% in oil, 2.3 g) was suspended in a mixed solvent of tetrahydrofuran (35 mL) and N,N-dimethylformamide (15 mL), and 3-aminobenzenethiol (5.0 g) was added dropwise at room temperature. The mixture was stirred at the same temperature for 5 min, iodoethane (6.86 g) was added, and the mixture was stirred for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a yellow oil (yield 5.0 g, 82%). was added dropwise at room temperature the mixture was stirred for 30 min the mixture was extracted with ethyl acetate The extract was washed with saturated brine dried over anhydrous sodium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

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

Procedure: To a suspension of 25 grams (0.193 mole; M.W. 125.19) of 3-aminothiophenol in 200 ml. of 5N sodium hydroxide was added, dropwise, over a period of 1 hour, a solution of 29.9 grams (0.193 mole) of ethyl iodide in 50 ml. of 1,4-dioxane. The resulting suspension was allowed to stir at room temperature for 1 hour, 200 ml. of ethyl ether were then added, and stirring was continued for an additional 30 minutes. The ether layer was separated, washed with a saturated aqueous solution of sodium bisulfite, dried over Na2SO4, and evaporated in vacuo to yield 28.10 grams of m-ethylthioaniline. stirring was continued for an additional 30 minutes The ether layer was separated washed with a saturated aqueous solution of sodium bisulfite dried over Na2SO4 evaporated in vacuo

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

Procedure: To a solution of 3-aminobenzenethiol (5.0 g, 39.9 mmol) in N,N-dimethylformamide (50 mL) was added potassium carbonate (6.62 g, 47.9 mmol) and iodoethane (3.19 mL, 39.9 mmol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate (3 times). The combined organic extracts were washed with brine (2 times), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes) to afford 3-(ethylthio)aniline (5.12 g, 84% yield). MS (m/z) 154.1 (M+H+). extracted with ethyl acetate (3 times) The combined organic extracts were washed with brine (2 times) dried over Na2SO4 filtered concentrated in vacuo The residue was purified via column chromatography (ISCO, 0-30% ethyl acetate/hexanes)