4-N-OCTYLANILINE

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:

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

Procedure: A 4.58-g portion (0.01 mole) of 2,4,6-triphenylpyrylium triflate is added to 200 ml of ethanol. To this solution, 2.05 g (0.01 mole) of p-n-octylaniline is added. The mixture is refluxed for about 20 hours. Upon removing the ethanol by rotating evaporation, an orange oil remains. To remove the last of the ethanol the oil is placed under high vacuum. The mixture is refluxed for about 20 hours Upon removing the ethanol evaporation To remove the last of the ethanol the oil

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

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

Procedure: A 10 ml methylene chloride solution of 1.0 g (5.09 mmol) of 2,4,6-trichloroaniline was added dropwise over 2 minutes to a 10 ml methylene chloride solution of 0.6 ml (4.97 mmol) of trichloromethyl chloroformate cooled to 5°-6° C. After stirring at 5°-6° C. for 2 hours, the mixture was added with 1.04 g (5.06 mmol) of 4-octylaniline and then stirred at room temperature for 16 hours. The reaction mixture was extracted with chloroform, and washed with an aqueous saturated solution of sodium hydrogen carbonate and an aqueous saturated solution of sodium chloride, successively. The organic layer was dried over anhydrous magnesium sulfate. After the removal of the solvent under reduced pressure, the residue was recrystallized from a mixed solvent of n-heptane and chloroform to give 0.95 g (43% yield) of 1-(4-octylphenyl)-3-(2,4,6-trichlorophenyl)urea, the physical properties of which being shown in the following Table 3. The compounds No. 4 and No. 11 listed in Table 3 were similarly prepared as above. cooled to 5°-6° C stirred at room temperature for 16 hours The reaction mixture was extracted with chloroform washed with an aqueous saturated solution of sodium hydrogen carbonate The organic layer was dried over anhydrous magnesium sulfate After the removal of the solvent under reduced pressure the residue was recrystallized from a mixed solvent of n-heptane and chloroform

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

Procedure: A 10 ml methylene chloride solution of 1.0 g (5.09 mmol) of 2,4,6-trichloroaniline was added dropwise over 2 minutes to a 10 ml methylene chloride solution of 0.6 ml (4.97 mmol) of trichloromethyl chloroformate cooled to 5°-6° C. After stirring at 5°-6° C. for 2 hours, the mixture was added with 1.04 g (5.06 mmol) of 4-octylaniline and then stirred at room temperature for 16 hours. The reaction mixture was extracted with chloroform, and washed with an aqueous saturated solution of sodium hydrogen carbonate and an aqueous saturated solution of sodium chloride, successively. The organic layer was dried over anhydrous magnesium sulfate. After the removal of the solvent under reduced pressure, the residue was recrystallized from a mixed solvent of n-heptane and chloroform to give 0.95 g (43% yield) of 1-(4-octylphenyl)-3-(2,4,6-trichlorophenyl)urea, the physical properties of which being shown in the following Table 3. The compounds No. 4 and No. 11 listed in Table 3 were similarly prepared as above. cooled to 5°-6° C stirred at room temperature for 16 hours The reaction mixture was extracted with chloroform washed with an aqueous saturated solution of sodium hydrogen carbonate The organic layer was dried over anhydrous magnesium sulfate After the removal of the solvent under reduced pressure the residue was recrystallized from a mixed solvent of n-heptane and chloroform

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

Procedure: To 10.6 ml (5.3 mmol) of a toluene solution of 0.50M 2,6-dichlorophenyl isocyanate was added 1.21 ml (5.32 mmol) of 4-octylaniline at room temperature and the whole was stirred for 16 hours. After removal of the solvent under reduced pressure, the residue was recrystallized from methanol to give 1.42 g (68% yield) of 1-(4-octylphenyl)-3-(2,6-dichlorophenyl)urea, the physical properties of which being shown in the following Table 3. The compounds No. 1, No. 13, No. 14, No. 17, and No. 18 listed in Table 3 were similarly prepared as above. After removal of the solvent under reduced pressure the residue was recrystallized from methanol

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

Procedure: To 10.6 ml (5.3 mmol) of a toluene solution of 0.50M 2,6-dichlorophenyl isocyanate was added 1.21 ml (5.32 mmol) of 4-octylaniline at room temperature and the whole was stirred for 16 hours. After removal of the solvent under reduced pressure, the residue was recrystallized from methanol to give 1.42 g (68% yield) of 1-(4-octylphenyl)-3-(2,6-dichlorophenyl)urea, the physical properties of which being shown in the following Table 3. The compounds No. 1, No. 13, No. 14, No. 17, and No. 18 listed in Table 3 were similarly prepared as above. After removal of the solvent under reduced pressure the residue was recrystallized from methanol

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

Procedure: 35 g (0.17M) of 4-octylaniline was cooled to 0° C. or below, 85 g of10% aqueous hydrochloric acid solution was added, and then a solution of 12.0 g of sodium nitrite in 68 ml of water was added. During the addition,the mixture was cooled so as not to exceed 0° C. After the addition,the mixture was allowed to react for 30 minutes, transferred into a dropping funnel and added dropwise into 170 g of an 8% NaOH aqueous solution containing 16 g of phenol held at 5° C. or below. After the addition, the mixture was stirred for 1 hour, and then 10% hydrochloric acid aqueous solution was added thereto until a pH of 5-6 to precipitate the reaction product. The precipitate was separated by filtration, washed with water, overnight under reduced pressure. After thedrying, the product was washed with 500 ml of petroleum ether and further dried under reduced pressure to obtain 30.8 g (0.10M) of 4-hydroxy-4'-octylazobenzene. The yield was 59%. During the addition,the mixture was cooled so as not to exceed 0° C to react for 30 minutes transferred into a dropping funnel held at 5° C. or below After the addition until a pH of 5-6 to precipitate the reaction product The precipitate was separated by filtration washed with water, overnight under reduced pressure After thedrying, the product was washed with 500 ml of petroleum ether further dried under reduced pressure