N-(2-phenoxyphenyl)acetamide

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: o-Nitrophenyl phenyl ether was reduced catalytically to o-phenoxyaniline, m. 43°-5°, which was acetylated to 2'-phenoxyacetanilide, m. 82°-4°. Yields from both reactions were essentially quantitative. The 2'-phenoxy-acetanilide was dissolved in acetic acid and treated at 60°-80° with red fuming nitric acid to produce a 60-70% yield of 4'-nitro-2'-phenoxy-acetanilide, m. 176°-183°. This was deacetylated by refluxing with methanolic hydrochloric acid to 4-nitro-2-phenoxyaniline, m. 116°-8°. The yield was 99% of theoretical. 43°-5°, which 82°-4° Yields from both reactions

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

Procedure: o-Nitrophenyl phenyl ether was reduced catalytically to o-phenoxyaniline, m. 43°-5°, which was acetylated to 2'-phenoxyacetanilide, m. 82°-4°. Yields from both reactions were essentially quantitative. The 2'-phenoxy-acetanilide was dissolved in acetic acid and treated at 60°-80° with red fuming nitric acid to produce a 60-70% yield of 4'-nitro-2'-phenoxy-acetanilide, m. 176°-183°. This was deacetylated by refluxing with methanolic hydrochloric acid to 4-nitro-2-phenoxyaniline, m. 116°-8°. The yield was 99% of theoretical. 43°-5°, which 82°-4° Yields from both reactions

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

Procedure: In 20 ml of nitrobenzene were refluxed 2.27 g of N-acetyl-2-phenoxyaniline, 1.3 ml of 2-iodoanisole, 1.38 g of potassium carbonate, 133 mg of a copper powder and 200 mg of copper bromide under heating for 8 hours. The reaction solution was cooled to room temperature, and after addition of ethyl acetate, the insoluble matter was removed by filtration. The filtrate was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 660 mg of N-acetyl-N-(2-methoxyphenyl)-2-phenoxyaniline as an oil. under heating for 8 hours the insoluble matter was removed by filtration The filtrate was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

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

Procedure: In 20 ml of nitrobenzene were refluxed 2.27 g of N-acetyl-2-phenoxyaniline, 1.3 ml of 2-iodoanisole, 1.38 g of potassium carbonate, 133 mg of a copper powder and 200 mg of copper bromide under heating for 8 hours. The reaction solution was cooled to room temperature, and after addition of ethyl acetate, the insoluble matter was removed by filtration. The filtrate was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 660 mg of N-acetyl-N-(2-methoxyphenyl)-2-phenoxyaniline as an oil. under heating for 8 hours the insoluble matter was removed by filtration The filtrate was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

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

Procedure: To a suspension of 400 mg of sodium hydride (60% in oil) in 30 ml of dimethylformamide was added 2.00 g of N-acetyl-2-phenoxyaniline at room temperature, followed by stirring at room temperature for 30 minutes. To the solution was added dropwise 1.64 g of 2-chlorobenzyl chloride at room temperature with stirring, followed by stirring for 30 minutes. After addition of ice-water, the reaction mixture was extracted with ether. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 2.92 g of N-acetyl-N-(2-chlorobenzyl)-2-phenoxyaniline as an oil. with stirring by stirring for 30 minutes the reaction mixture was extracted with ether The extract was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

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

Procedure: To a solution of 28.5 g of 2-phenoxyaniline and 25.8 ml of triethylamine in 250 ml of methylene chloride was added dropwise 11.5 ml of acetyl chloride under ice-cooling. After stirring at room temperature for 1.5 hours, the reaction mixture was concentrated under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 33.7 g of N-acetyl-2-phenoxyaniline. cooling the reaction mixture was concentrated under reduced pressure the residue was poured into water extracted with ethyl acetate The extract was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

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

Procedure: To a solution of 28.5 g of 2-phenoxyaniline and 25.8 ml of triethylamine in 250 ml of methylene chloride was added dropwise 11.5 ml of acetyl chloride under ice-cooling. After stirring at room temperature for 1.5 hours, the reaction mixture was concentrated under reduced pressure, and the residue was poured into water and extracted with ethyl acetate. The extract was washed with 0.5 N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the solvent was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4) to give 33.7 g of N-acetyl-2-phenoxyaniline. cooling the reaction mixture was concentrated under reduced pressure the residue was poured into water extracted with ethyl acetate The extract was washed with 0.5 N hydrochloric acid a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution, successively, and dried over anhydrous sodium sulfate After removal of the drying agent by filtration the solvent was concentrated under reduced pressure the residue was purified by silica gel column chromatography (eluent; ethyl acetate−hexane=1:4)

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