N-N-PENTYLANILINE

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

実験手順: p-Toluenesulfinic acid (188 ml, 1.20 mmol) was added at room temperature to a solution of N-allyl-N-pentylphenylamine(221 mg, 1.08 mmol) and tetrakis(triphenylphosphine)palladium(87.8 mg, 75.9 μmol) in dichloromethane(11 ml). The reaction mixture was stirred at room temperature for 60 minutes and saturated aqueous sodium hydrogen carbonate(6.8 ml) was added. After stirred for 5 minutes, the mixture was extracted with ether(80 ml). The extract was dried on magnesium sulfate, filterd and concentrated in vacuum. The residue was chromatographed on silica gel to give N-pentylphenylamine(164 mg) in 93% yield as a colorless oil. After stirred for 5 minutes the mixture was extracted with ether(80 ml) The extract was dried on magnesium sulfate, filterd concentrated in vacuum The residue was chromatographed on silica gel

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

実験手順: A solution of 4.05 g (24.8 mmole) of N-Pentylaniline (from Step A) in 45 ml of toluene an 8.96 ml (24.8 mmole) of 2.77N NaOH were mechanically stirred at -5° C., and 25.7 ml (49.6 mmole) of 1.93M phosgene in toluene was added dropwise over 30 minutes while maintaining -5°. After half the phosgene solution had been added, the rate of addition was increased easily. After stirring at -5° for an additional 30 minutes, the phases were separated and the toluene layer was dried over 10 g of solid sodium chloride. Concentration gave 5.5 g (98%) of dark yellow oil. while maintaining -5° the rate of addition was increased easily the phases were separated the toluene layer was dried over 10 g of solid sodium chloride Concentration

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

実験手順: p-Toluenesulfinic acid (188 ml, 1.20 mmol) was added at room temperature to a solution of N-allyl-N-pentylphenylamine(221 mg, 1.08 mmol) and tetrakis(triphenylphosphine)palladium(87.8 mg, 75.9 μmol) in dichloromethane(11 ml). The reaction mixture was stirred at room temperature for 60 minutes and saturated aqueous sodium hydrogen carbonate(6.8 ml) was added. After stirred for 5 minutes, the mixture was extracted with ether(80 ml). The extract was dried on magnesium sulfate, filterd and concentrated in vacuum. The residue was chromatographed on silica gel to give N-pentylphenylamine(164 mg) in 93% yield as a colorless oil. After stirred for 5 minutes the mixture was extracted with ether(80 ml) The extract was dried on magnesium sulfate, filterd concentrated in vacuum The residue was chromatographed on silica gel

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

実験手順: p-Toluenesulfinic acid (188 ml, 1.20 mmol) was added at room temperature to a solution of N-allyl-N-pentylphenylamine(221 mg, 1.08 mmol) and tetrakis(triphenylphosphine)palladium(87.8 mg, 75.9 μmol) in dichloromethane(11 ml). The reaction mixture was stirred at room temperature for 60 minutes and saturated aqueous sodium hydrogen carbonate(6.8 ml) was added. After stirred for 5 minutes, the mixture was extracted with ether(80 ml). The extract was dried on magnesium sulfate, filterd and concentrated in vacuum. The residue was chromatographed on silica gel to give N-pentylphenylamine(164 mg) in 93% yield as a colorless oil. After stirred for 5 minutes the mixture was extracted with ether(80 ml) The extract was dried on magnesium sulfate, filterd concentrated in vacuum The residue was chromatographed on silica gel

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

実験手順: A solution of 4.05 g (24.8 mmole) of N-pentylaniline (from Step A) in 45 ml of toluene and 8.96 ml (24.8 mmole) of 2.77N NaOH were mechanically stirred at -5° C., and 25.7 ml (49.6 mmole) of 1.93M phosgene in toluene was added dropwise over 30 minutes while maintaining -5°. After half the phosgene solution had been added, the rate of addition was increased easily. After stirring at -5° for an additional 30 minutes, the phases were separated and the toluene layer was dried over 10 g of solid sodium chloride. Concentration gave 5.5 g (98%) of dark yellow oil. while maintaining -5° the rate of addition was increased easily the phases were separated the toluene layer was dried over 10 g of solid sodium chloride Concentration

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

実験手順: A solution of 4.05 g (24.8 mmole) of N-pentylaniline (from Step A) in 45 ml of toluene and 8.96 ml (24.8 mmole) of 2.77N NaOH were mechanically stirred at -5° C., and 25.7 ml (49.6 mmole) of 1.93M phosgene in toluene was added dropwise over 30 minutes while maintaining -5°. After half the phosgene solution had been added, the rate of addition was increased easily. After stirring at -5° for an additional 30 minutes, the phases were separated and the toluene layer was dried over 10 g of solid sodium chloride. Concentration gave 5.5 g (98%) of dark yellow oil. while maintaining -5° the rate of addition was increased easily the phases were separated the toluene layer was dried over 10 g of solid sodium chloride Concentration

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

実験手順: A solution of 4.05 g (24.8 mmole) of N-pentylaniline (from Step A) in 45 ml of toluene and 8.96 ml (24.8 mmole) of 2.77N NaOH were mechanically stirred at -5° C., and 25.7 ml (49.6 mmole) of 1.93M phosgene in toluene was added dropwise over 30 minutes while maintaining -5°. After half the phosgene solution had been added, the rate of addition was increased easily. After stirring at -5° for an additional 30 minutes, the phases were separated and the toluene layer was dried over 10 g of solid sodium chloride. Concentration gave 5.5 g (98%) of dark yellow oil. while maintaining -5° the rate of addition was increased easily the phases were separated the toluene layer was dried over 10 g of solid sodium chloride Concentration

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

実験手順: A solution of 4.05 g (24.8 mmole) of N-Pentylaniline (from Step A) in 45 ml of toluene an 8.96 ml (24.8 mmole) of 2.77N NaOH were mechanically stirred at -5° C., and 25.7 ml (49.6 mmole) of 1.93M phosgene in toluene was added dropwise over 30 minutes while maintaining -5°. After half the phosgene solution had been added, the rate of addition was increased easily. After stirring at -5° for an additional 30 minutes, the phases were separated and the toluene layer was dried over 10 g of solid sodium chloride. Concentration gave 5.5 g (98%) of dark yellow oil. while maintaining -5° the rate of addition was increased easily the phases were separated the toluene layer was dried over 10 g of solid sodium chloride Concentration