1-(4-chlorophenyl)imidazolidin-2-one

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

Procedure: In a solution of glacial acetic acid (2750 ml) and water (250 ml) was dissolved 150 g (0.75 mol) of 1-(4-chlorophenyl)-2-imidazolidinone with heating. The solution was cooled to room temperature, and sodium nitrite (70 g, 1.0 mol) in water (200 ml) was added dropwise over 1 hour. The mixture was stirred for another 6 hours, diluted with water (1.5 l.) and the product (137 g, 81%) was collected, m.p. 154°-156°. with heating the product (137 g, 81%) was collected

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

Procedure: In a solution of glacial acetic acid (2750 ml) and water (250 ml) was dissolved 150 g (0.75 mol) of 1-(4-chlorophenyl)-2-imidazolidinone with heating. The solution was cooled to room temperature, and sodium nitrite (70 g, 1.0 mol) in water (200 ml) was added dropwise over 1 hour. The mixture was stirred for another 6 hours, diluted with water (1.5 l.) and the product (137 g, 81%) was collected, m.p. 154°-156°. with heating the product (137 g, 81%) was collected

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

Procedure: To a solution of 1-(4-chlorophenyl)-2-imidazolidinone (0.10 g, 0.53 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.3 mg, 0.80 mmol). The mixture was stirred at room temperature for 30 min and then cooled in ice bath. 1-{3-[(5-Bromopentyl)oxy]propoxy}-4-methoxybenzene (0.18 g, 0.53 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. 5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 6) as a white solid (0.16 g, 68%). cooled in an ice bath cooled in ice bath the mixture was stirred at room temperature for additional 4 hours The reaction was quenched with MeOH 5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue The dichloromethane layer was separated dried over MgSO4 filtered evaporated purified by column chromatography (ethyl acetate:MeOH=10:1)

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

Procedure: To a solution of 1-(4-chlorophenyl)-2-imidazolidinone (0.10 g, 0.53 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.3 mg, 0.80 mmol). The mixture was stirred at room temperature for 30 min and then cooled in ice bath. 1-{3-[(5-Bromopentyl)oxy]propoxy}-4-methoxybenzene (0.18 g, 0.53 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. 5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 6) as a white solid (0.16 g, 68%). cooled in an ice bath cooled in ice bath the mixture was stirred at room temperature for additional 4 hours The reaction was quenched with MeOH 5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue The dichloromethane layer was separated dried over MgSO4 filtered evaporated purified by column chromatography (ethyl acetate:MeOH=10:1)

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

Procedure: In a solution of glacial acetic acid (2750 ml) and water (250 ml) was dissolved 150 g (0.75 mol) of 1-(4-chlorophenyl)-2-imidazolidinone with heating. The solution was cooled to room temperature, and sodium nitrite (70 g, 1.0 mol) in water (200 ml) was added dropwise over 1 hr. The mixture was stirred for another 6 hrs, diluted with water (1.5 l) and the product (137 g, 81%) was collected m.p. 154°-156°. with heating the product (137 g, 81%) was collected m.p. 154°-156°

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

Procedure: A reaction was conducted in a manner similar to Referential Example 13 by using 1-(4-chlorophenyl)-2-imidazolidinone (Compound No. 2) in place of 1-(4-ethylphenyl)-2-imidazolidinone (Compound No. 1) and 4-(3-chloropropoxy)benzaldehyde in lieu of 4-(2-chloroethoxy)benzaldehyde, whereby the title compound was obtained in a yield of 34%.

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

Procedure: In a solution of glacial acetic acid (2750 ml) and water (250 ml) was dissolved 150 g (0.75 mol) of 1-(4-chlorophenyl)-2-imidazolidinone with heating. The solution was cooled to room temperature, and sodium nitrite (70 g, 1.0 mol) in water (200 ml) was added dropwise over 1 hour. The mixture was stirred for another 6 hours, diluted with water (1.5 l.) and the product (137 g, 81%) was collected, m.p. 154°-156°. with heating the product (137 g, 81%) was collected

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

Procedure: To a solution of 1-(4-chlorophenyl)-2-imidazolidinone (0.10 g, 0.53 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 27.3 mg, 0.80 mmol). The mixture was stirred at room temperature for 30 min and then cooled in ice bath. 1-{3-[(5-Bromopentyl)oxy]propoxy}-4-methoxybenzene (0.18 g, 0.53 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. 5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 6) as a white solid (0.16 g, 68%). cooled in an ice bath cooled in ice bath the mixture was stirred at room temperature for additional 4 hours The reaction was quenched with MeOH 5 mL saturated aqueous NH4Cl solution and 10 mL dichloromethane were successively added to the residue The dichloromethane layer was separated dried over MgSO4 filtered evaporated purified by column chromatography (ethyl acetate:MeOH=10:1)