N-butyl-2-phenylacetamide

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Butyl-phenylacetamide (1.80 g, 0.0094 m) in N-methyl pyrrolidone (10 ml) was stirred at 80° C. under nitrogen during the portionwise addition of a 50% sodium hydride/oil dispersion (0.75 g, 0.0094 m). After the addition, the mixture was warmed to 100° C. and 2-cyclohexylsulphinyl-4-methyloxazole (2.0 g, 0.0094 m) in dry N-methyl pyrrolidone (10 ml) was added. The mixture was stirred at 100° C. for 5 hours and then hydrolysed with water. The solvent was removed in vacuo and the product isolated by column chromatography on silica using ether. Distillation gave the title product as a colourless oil. b.p. 126°-130° C./0.2 mm. After the addition The solvent was removed in vacuo the product isolated by column chromatography on silica Distillation

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Butyl-phenylacetamide (1.80 g, 0.0094 m) in N-methyl pyrrolidone (10 ml) was stirred at 80° C. under nitrogen during the portionwise addition of a 50% sodium hydride/oil dispersion (0.75 g, 0.0094 m). After the addition, the mixture was warmed to 100° C. and 2-cyclohexylsulphinyl-4-methyloxazole (2.0 g, 0.0094 m) in dry N-methyl pyrrolidone (10 ml) was added. The mixture was stirred at 100° C. for 5 hours and then hydrolysed with water. The solvent was removed in vacuo and the product isolated by column chromatography on silica using ether. Distillation gave the title product as a colourless oil. b.p. 126°-130° C./0.2 mm. After the addition The solvent was removed in vacuo the product isolated by column chromatography on silica Distillation

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

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

Procedure: Phenylacetic acid (16 g, 117.6 mmol) and methanol (60 ml) were added to a 250 ml three-necked flask, followed by addition of 5 drops of concentrated sulphuric acid. The resulting solution was heated to reflux for 6 hours. Then, the mixture was cooled to room temperature, followed by adding n-butylamine (12 ml, 121.4 mmol), and heated to reflux for another 3 hours. After the reaction was completed, it was cooled to room temperature. Most of the solvent was removed by rotary vacuum evaporation, 30 ml of water was added thereinto, and the mixture was extracted with ethyl acetate (3×80 ml). The combined organic layer was dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure to yield 15.9 g of N-n-butylphenylacetamide (white solid, yield: 70.4%). The resulting solution was heated to reflux for 6 hours heated to reflux for another 3 hours it was cooled to room temperature Most of the solvent was removed by rotary vacuum evaporation, 30 ml of water was added the mixture was extracted with ethyl acetate (3×80 ml) The combined organic layer was dried over anhydrous magnesium sulfate filtrated concentrated under reduced pressure

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-Butyl-phenylacetamide (1.80 g, 0.0094 m) in N-methyl pyrrolidone (10 ml) was stirred at 80° C. under nitrogen during the portionwise addition of a 50% sodium hydride/oil dispersion (0.75 g, 0.0094 m). After the addition, the mixture was warmed to 100° C. and 2-cyclohexylsulphinyl-4-methyloxazole (2.0 g, 0.0094 m) in dry N-methyl pyrrolidone (10 ml) was added. The mixture was stirred at 100° C. for 5 hours and then hydrolysed with water. The solvent was removed in vacuo and the product isolated by column chromatography on silica using ether. Distillation gave the title product as a colourless oil. b.p. 126°-130° C./0.2 mm. After the addition The solvent was removed in vacuo the product isolated by column chromatography on silica Distillation