2-(4-chlorophenyl)ethanethioamide

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 mixture of allyl 4-(bromoacetyl)piperidine-1-carboxylate (547 mg) and 2-(4-chlorophenyl)ethanethioamide (366 mg) in ethanol (15 ml) was refluxed for 5 hours. The reaction mixture was evaporated to dryness and the residue was purified by chromatography on silica eluting with methanol/dichloromethane (2:98) to give allyl 4-[2-(4-chlorobenzyl)-1,3-thiazol-4-yl]piperidine-1-carboxylate. Yield 698 mg. NMR (CDCl3): 1.65 (m, 2H), 2.25 (m, 2H), 2.95 (m, 2H), 3.2 (m, 1H), 4.3 (m, 2H), 4.55 (m, 4H), 5.3 (m, 2H), 6.0 (m, 1H), 6.95 (s, 1H), 7.35 (m, 4H). was refluxed for 5 hours The reaction mixture was evaporated to dryness the residue was purified by chromatography on silica eluting with methanol/dichloromethane (2:98)

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

Procedure: A solution of 4-chlorophenyl(thioacetamide) (14.8 g.) and methyl iodide (32 g.) in acetone (40 ml.) was heated to reflux for 20 minutes. The mixture was cooled and filtered to give pure methyl 4-chlorophenyl(thioacetimidate) hydriodide, m.p. 172°-174°. to reflux for 20 minutes The mixture was cooled filtered

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(4-chlorophenyl)thioacetamide (3.51 g) in 1,4-dioxane (20 mL) were added dichloroacetone (2.64 g) and sodium hydrogen carbonate (1.75 g) at room temperature, and the mixture was stirred for 3 days. Insoluble material was removed by filtration, thionyl chloride (1.52 mL) was added to the filtrate, and the mixture was heated at 70° C. for 30 min. The reaction mixture was adjusted to pH=8-9 by the addition of saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate/hexane (1/1)(100 mL×2). The organic layer was washed with saturated brine, and concentrated under reduced pressure to give the title compound (4.19 g) as a pale-yellow solid. Insoluble material was removed by filtration, thionyl chloride (1.52 mL) was added to the filtrate The reaction mixture was adjusted to pH=8-9 by the addition of saturated aqueous sodium hydrogen carbonate solution extracted with ethyl acetate/hexane (1/1)(100 mL×2) The organic layer was washed with saturated brine concentrated under reduced pressure