N-(4-chlorophenyl)acetamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In one example, under nitrogen gas, a stirred mixture of 4-Chloro-1-nitrobenzene (e.g., about 1 g, 6.35 mmol), thioacetic acid (e.g., about 1.93 g, 25.39 mmol), K2CO3 (e.g., about 0.050 g, 0.36 mmol), and dry Triton-X 405 (e.g., about 0.010 g) were heated at about 150° C. The progress of the reaction was monitored by HPLC and GC. After four hours the reaction was cooled to room temperature, and acetone (e.g., about 8 mL) was added and filtered through a sintered glass funnel. Evaporation of the acetone produced about 0.975 g of N-(4-Chloro-phenyl)-acetamide (e.g., about 91%). dry Triton-X 405 (e.g., about 0.010 g) After four hours the reaction was cooled to room temperature acetone (e.g., about 8 mL) was added filtered through a sintered glass funnel Evaporation of the acetone

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In one example, under nitrogen gas, a stirred mixture of 4-Chloro-1-nitrobenzene (e.g., about 1 g, 6.35 mmol), thioacetic acid (e.g., about 1.93 g, 25.39 mmol), K2CO3 (e.g., about 0.050 g, 0.36 mmol), and dry Triton-X 405 (e.g., about 0.010 g) were heated at about 150° C. The progress of the reaction was monitored by HPLC and GC. After four hours the reaction was cooled to room temperature, and acetone (e.g., about 8 mL) was added and filtered through a sintered glass funnel. Evaporation of the acetone produced about 0.975 g of N-(4-Chloro-phenyl)-acetamide (e.g., about 91%). dry Triton-X 405 (e.g., about 0.010 g) After four hours the reaction was cooled to room temperature acetone (e.g., about 8 mL) was added filtered through a sintered glass funnel Evaporation of the acetone

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

実験手順: Methyl 2-(4-iodophenyl)propionate (2 g.), acet-p-chloroanilide (1.17 g.), potassium carbonate (0.62 g.) and copper powder (0.1 g.) were heated at 165°C. for 7.5 hours. The cooled solid was triturated with methylene chloride, filtered, and the filtrate evaporated to dryness. The residue was refluxed for 1.5 hours with ethanol (7 ml.) and 2.5N sodium hydroxide (14 ml.); ethanol was distilled in vacuo and the residue diluted with water, washed with ether and acidified with dilute hydrochloric acid. The resulting oil was isolated in ether and evaporated to dryness. The resulting gum was purified by preparative layer chromatography using 5% acetic acid/petroleum ether b.p. 62°-68°C. and eluting with ethyl acetate; recrystallization from benzene/petroleum ether b.p. 62°-68°C. and from petroleum ether b.p. 80°-100°C. gave 2-[4-(4-chloroanilino)-phenyl]propionic acid, m.p. 106-109°C. The cooled solid was triturated with methylene chloride filtered the filtrate evaporated to dryness The residue was refluxed for 1.5 hours with ethanol (7 ml.) and 2.5N sodium hydroxide (14 ml.) ethanol was distilled in vacuo the residue diluted with water washed with ether The resulting oil was isolated in ether evaporated to dryness The resulting gum was purified by preparative layer chromatography eluting with ethyl acetate recrystallization from benzene/petroleum ether b.p. 62°-68°C.

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

実験手順: Following the general procedure, 4-chloroacetanilide (85 mg, 0.5 mmol) was coupled with p-toluidine (80 mg, 0.75 mmol) with the reaction temperature of 90° C. and the reaction time of 14 h. Chromatography on silica gel column with 2:1 hexane:ethyl acetate gave 118 mg (98%) of the title compound as a pink solid. the reaction time of 14 h

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In one example, under nitrogen gas, a stirred mixture of 4-Chloro-1-nitrobenzene (e.g., about 1 g, 6.35 mmol), thioacetic acid (e.g., about 1.93 g, 25.39 mmol), K2CO3 (e.g., about 0.050 g, 0.36 mmol), and dry Triton-X 405 (e.g., about 0.010 g) were heated at about 150° C. The progress of the reaction was monitored by HPLC and GC. After four hours the reaction was cooled to room temperature, and acetone (e.g., about 8 mL) was added and filtered through a sintered glass funnel. Evaporation of the acetone produced about 0.975 g of N-(4-Chloro-phenyl)-acetamide (e.g., about 91%). dry Triton-X 405 (e.g., about 0.010 g) After four hours the reaction was cooled to room temperature acetone (e.g., about 8 mL) was added filtered through a sintered glass funnel Evaporation of the acetone