N-phenacylacetamide

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:

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

Procedure: Thiosemicarbazide (1.98 g, 20 mmol) was added to a solution of N-(2-oxo-2-phenyl-ethyl)-acetamide (3.84 g, 20 mmol, prepared in the previous step, in 70 ml of methanol plus 5.4 ml of 1N HCl plus 5.0 ml of water and the reaction stirred at room temperature overnight. The solid formed was collected by filtration and dried to give 3.9 g (78%) of the title compound as a white solid, mp 208-211° C. The solid formed was collected by filtration dried

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

Procedure: A mixture of N-(2-hydroxy-2-phenyl-ethyl)-acetamide (7.68 g, 43 mmol), prepared in the previous step, and pyridinium chlorochromate (14.0 g, 65 mmol) in 800 ml of methylene chloride was stirred at room temperature for 5 hours. The organic phase was decanted from a black oily residue in the flask. This black residue was triturated with methylene chloride and then with 10% methanol-methylene chloride. The organic phases were concentrated under reduced pressure and the residue chromatographed on 400 g of silica gel (230-400 mesh) using ethyl acetate-methylene chloride as the eluent. Isolation of the desired component gave N-(2-oxo-2-phenyl-ethyl)-acetamide (4.0 g, 53%) as a white solid. The material was used in the following reaction without additional purification, MS m/e (M+H)+ 178. The organic phase was decanted from a black oily residue in the flask This black residue was triturated with methylene chloride The organic phases were concentrated under reduced pressure the residue chromatographed on 400 g of silica gel (230-400 mesh)

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

Procedure: A mixture of N-(2-hydroxy-2-phenyl-ethyl)-acetamide (7.68 g, 43 mmol), prepared in the previous step, and pyridinium chlorochromate (14.0 g, 65 mmol) in 800 ml of methylene chloride was stirred at room temperature for 5 hours. The organic phase was decanted from a black oily residue in the flask. This black residue was triturated with methylene chloride and then with 10% methanol-methylene chloride. The organic phases were concentrated under reduced pressure and the residue chromatographed on 400 g of silica gel (230-400 mesh) using ethyl acetate-methylene chloride as the eluent. Isolation of the desired component gave N-(2-oxo-2-phenyl-ethyl)-acetamide (4.0 g, 53%) as a white solid. The material was used in the following reaction without additional purification, MS m/e (M+H)+ 178. The organic phase was decanted from a black oily residue in the flask This black residue was triturated with methylene chloride The organic phases were concentrated under reduced pressure the residue chromatographed on 400 g of silica gel (230-400 mesh)

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

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

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