1,3-diazaspiro[4.5]decane-2,4-dione

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-diazaspiro[4,5]decane-2,4-dione (4.0 g 0.078 mole) J. Prakt. Chem. 141 5-43 (1934) was added to a suspension of sodium hydride (1.14 g 50% oil dispersion) in dimethylformamide and heated at 50° C. for 1 hour, cooled, methyl iodide added (1.63 ml. 1.1 eq) and the mixture heated at 50° C. The dimethylformamide was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic extract was washed with water, dried (MgSO4), evaporated to dryness and the crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.) to give the title compound as white prisms m.p. 214°-215° C. Yield 2.6 g=39%. cooled the mixture heated at 50° C The dimethylformamide was removed under reduced pressure the residue partitioned between ethyl acetate and brine The organic extract was washed with water dried (MgSO4) evaporated to dryness the crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-diazaspiro[4,5]decane-2,4-dione (4.0 g 0.078 mole) J. Prakt. Chem. 141 5-43 (1934) was added to a suspension of sodium hydride (1.14 g 50% oil dispersion) in dimethylformamide and heated at 50° C. for 1 hour, cooled, methyl iodide added (1.63 ml. 1.1 eq) and the mixture heated at 50° C. The dimethylformamide was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic extract was washed with water, dried (MgSO4), evaporated to dryness and the crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.) to give the title compound as white prisms m.p. 214°-215° C. Yield 2.6 g=39%. cooled the mixture heated at 50° C The dimethylformamide was removed under reduced pressure the residue partitioned between ethyl acetate and brine The organic extract was washed with water dried (MgSO4) evaporated to dryness the crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.)

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

Procedure: 5,5-Pentamethylenehydantoin (2.00 g) was dissolved in tetrahydrofuran (10 mL), and sodium hydride (60%, in oil) (0.49 g) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 1-naphthoyl chloride (2.33 g) was added at 0° C., and the mixture was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate (100 mL) was added to the reaction solution, and the solution was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain the white solid. Further recrystallization with IPE and ethyl acetate afforded 1.87 g of white crystals. cooling the mixture was stirred at room temperature overnight After the solvent was distilled off ethyl acetate (100 mL) was added to the reaction solution the solution was washed with 1N hydrochloric acid After drying over anhydrous magnesium sulfate the solvent was distilled off to obtain the white solid Further recrystallization with IPE and ethyl acetate

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

Procedure: 5,5-Pentamethylenehydantoin (2.00 g) was dissolved in tetrahydrofuran (10 mL), and sodium hydride (60%, in oil) (0.49 g) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 1-naphthoyl chloride (2.33 g) was added at 0° C., and the mixture was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate (100 mL) was added to the reaction solution, and the solution was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain the white solid. Further recrystallization with IPE and ethyl acetate afforded 1.87 g of white crystals. cooling the mixture was stirred at room temperature overnight After the solvent was distilled off ethyl acetate (100 mL) was added to the reaction solution the solution was washed with 1N hydrochloric acid After drying over anhydrous magnesium sulfate the solvent was distilled off to obtain the white solid Further recrystallization with IPE and ethyl acetate

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-diazaspiro[4,5]decane-2,4-dione (4.0 g 0.078 mole) J. Prakt. Chem. 141 5-43 (1934) was added to a suspension of sodium hydride (1.14 g 50% oil dispersion) in dimethylformamide and heated at 50° C. for 1 hour, cooled, methyl iodide added (1.63 ml. 1.1 eq) and the mixture heated at 50° C. The dimethylformamide was removed under reduced pressure and the residue partitioned between ethyl acetate and brine. The organic extract was washed with water, dried (MgSO4), evaporated to dryness and the crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.) to give the title compound as white prisms m.p. 214°-215° C. Yield 2.6 g=39%. cooled the mixture heated at 50° C The dimethylformamide was removed under reduced pressure the residue partitioned between ethyl acetate and brine The organic extract was washed with water dried (MgSO4) evaporated to dryness the crystalline residue crystallised from ethyl acetate-light petroleum (40°-60° C.)

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

Procedure: 5,5-Pentamethylenehydantoin (2.00 g) was dissolved in tetrahydrofuran (10 mL), and sodium hydride (60%, in oil) (0.49 g) was added at 0° C. under ice-cooling. After stirred for 30 minutes, 1-naphthoyl chloride (2.33 g) was added at 0° C., and the mixture was stirred at room temperature overnight. After the solvent was distilled off, ethyl acetate (100 mL) was added to the reaction solution, and the solution was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn. After drying over anhydrous magnesium sulfate, the solvent was distilled off to obtain the white solid. Further recrystallization with IPE and ethyl acetate afforded 1.87 g of white crystals. cooling the mixture was stirred at room temperature overnight After the solvent was distilled off ethyl acetate (100 mL) was added to the reaction solution the solution was washed with 1N hydrochloric acid After drying over anhydrous magnesium sulfate the solvent was distilled off to obtain the white solid Further recrystallization with IPE and ethyl acetate