3-[2-(4-chlorophenyl)-2-oxoethyl]-1,3-thiazolidine-2,4-dione

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: Butylhydrazine oxalate (41 g, 230 mmol) and 40 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione (161 mmol) in 2200 mL of methanol were cooled in an ice bath and treated with 30.3 g (300 mmol) of triethylamine. The reaction mixture was stirred at room temperature for 30 minutes, then refluxed overnight. The reaction mixture was cooled and 400 mL of water was added. This mixture was extracted with ethyl acetate. The organic phase was washed twice with 10% aqueous sodium hydroxide solution, then dried and stripped. The solids obtained were recrystallized from ethyl acetate/hexane to give 9.6 g of 2-n-butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one. refluxed overnight The reaction mixture was cooled This mixture was extracted with ethyl acetate The organic phase was washed twice with 10% aqueous sodium hydroxide solution dried The solids obtained were recrystallized from ethyl acetate/hexane

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

Procedure: Butylhydrazine oxalate (41 g, 230 mmol) and 40 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione (161 mmol) in 2200 mL of methanol were cooled in an ice bath and treated with 30.3 g (300 mmol) of triethylamine. The reaction mixture was stirred at room temperature for 30 minutes, then refluxed overnight. The reaction mixture was cooled and 400 mL of water was added. This mixture was extracted with ethyl acetate. The organic phase was washed twice with 10% aqueous sodium hydroxide solution, then dried and stripped. The solids obtained were recrystallized from ethyl acetate/hexane to give 9.6 g of 2-n-butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one. refluxed overnight The reaction mixture was cooled This mixture was extracted with ethyl acetate The organic phase was washed twice with 10% aqueous sodium hydroxide solution dried The solids obtained were recrystallized from ethyl acetate/hexane

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

Procedure: Hydrazine hydrate (8.0 g, 160 mmol) and 19.55 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione in 100 mL of methanol were stirred at room temperature over a weekend, then refluxed for 8 hours. The reaction mixture was cooled and the solids were filtered, washed with methanol and dried to give 9.06 g of white solid 6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one (57% yield). refluxed for 8 hours The reaction mixture was cooled the solids were filtered washed with methanol dried

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

Procedure: To a suspension of 3.15 g of sodium hydride (60% in mineral oil, 78.8 mmol) in 70 mL of DMF at 0° C. was added 9.76 g (75 mmol) of 2,4-thiazolidinedione portion-wise. The reaction mixture was stirred for 20 minutes, then 17.5 g of 2-bromo-4′-chloroacetophenone (75 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 5 hours. Ethyl acetate and water were added, the organic phase was separated, and washed with water and brine. The combined aqueous extracts were washed with additional ethyl acetate which was then washed with water and brine and combined with the rest of the organic layer. The ethyl acetate phases were dried over magnesium sulfate, filtered and stripped to give 23 g of crude product. Recrystallization from 1:1 toluene:hexane gave 16.25 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione, (85% yield) mp 122–124° C. stirred for 5 hours the organic phase was separated washed with water and brine The combined aqueous extracts were washed with additional ethyl acetate which was then washed with water and brine The ethyl acetate phases were dried over magnesium sulfate filtered to give 23 g of crude product Recrystallization from 1:1 toluene

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

Procedure: To a suspension of 3.15 g of sodium hydride (60% in mineral oil, 78.8 mmol) in 70 mL of DMF at 0° C. was added 9.76 g (75 mmol) of 2,4-thiazolidinedione portion-wise. The reaction mixture was stirred for 20 minutes, then 17.5 g of 2-bromo-4′-chloroacetophenone (75 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 5 hours. Ethyl acetate and water were added, the organic phase was separated, and washed with water and brine. The combined aqueous extracts were washed with additional ethyl acetate which was then washed with water and brine and combined with the rest of the organic layer. The ethyl acetate phases were dried over magnesium sulfate, filtered and stripped to give 23 g of crude product. Recrystallization from 1:1 toluene:hexane gave 16.25 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione, (85% yield) mp 122–124° C. stirred for 5 hours the organic phase was separated washed with water and brine The combined aqueous extracts were washed with additional ethyl acetate which was then washed with water and brine The ethyl acetate phases were dried over magnesium sulfate filtered to give 23 g of crude product Recrystallization from 1:1 toluene

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

Procedure: Butylhydrazine oxalate (41 g, 230 mmol) and 40 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione (161 mmol) in 2200 mL of methanol were cooled in an ice bath and treated with 30.3 g (300 mmol) of triethylamine. The reaction mixture was stirred at room temperature for 30 minutes, then refluxed overnight. The reaction mixture was cooled and 400 mL of water was added. This mixture was extracted with ethyl acetate. The organic phase was washed twice with 10% aqueous sodium hydroxide solution, then dried and stripped. The solids obtained were recrystallized from ethyl acetate/hexane to give 9.6 g of 2-n-butyl-6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one. refluxed overnight The reaction mixture was cooled This mixture was extracted with ethyl acetate The organic phase was washed twice with 10% aqueous sodium hydroxide solution dried The solids obtained were recrystallized from ethyl acetate/hexane

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

Procedure: Hydrazine hydrate (8.0 g, 160 mmol) and 19.55 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione in 100 mL of methanol were stirred at room temperature over a weekend, then refluxed for 8 hours. The reaction mixture was cooled and the solids were filtered, washed with methanol and dried to give 9.06 g of white solid 6-(4-chlorophenyl)-4,5-dihydro-1,2,4-triazin-3-one (57% yield). refluxed for 8 hours The reaction mixture was cooled the solids were filtered washed with methanol dried

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

Procedure: To a suspension of 3.15 g of sodium hydride (60% in mineral oil, 78.8 mmol) in 70 mL of DMF at 0° C. was added 9.76 g (75 mmol) of 2,4-thiazolidinedione portion-wise. The reaction mixture was stirred for 20 minutes, then 17.5 g of 2-bromo-4′-chloroacetophenone (75 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 5 hours. Ethyl acetate and water were added, the organic phase was separated, and washed with water and brine. The combined aqueous extracts were washed with additional ethyl acetate which was then washed with water and brine and combined with the rest of the organic layer. The ethyl acetate phases were dried over magnesium sulfate, filtered and stripped to give 23 g of crude product. Recrystallization from 1:1 toluene:hexane gave 16.25 g of 3-(2-(4-chlorophenyl)-2-oxo-ethyl)-thiazolidine-2,4-dione, (85% yield) mp 122–124° C. stirred for 5 hours the organic phase was separated washed with water and brine The combined aqueous extracts were washed with additional ethyl acetate which was then washed with water and brine The ethyl acetate phases were dried over magnesium sulfate filtered to give 23 g of crude product Recrystallization from 1:1 toluene