3-(3-chloropropyl)-1,3-oxazolidin-2-one

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 % of 2-nitroimidazole (53 mmol) and 7.32 % of KzCO3 was heated at 60° C. for 0.5 hours. Then 8.6 % (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955)) was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-3-(2-nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone; mp 89°-91° C. The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-nitroimidazole (53 mmol) and 7.32 g of K2CO3 was heated at 60° C. for 0.5 hours. Then 8.6 g (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955), was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-[3-(2-nitro-1H-imidazol-1-yl) propyl]-2-oxazolidinone; mp 89°-91° C. , 13, 565 (1955), was added The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-nitroimidazole (53 mmol) and 7.32 g of K2CO3 was heated at 60° C. for 0.5 hours. Then 8.6 g (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955), was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-[3-(2-nitro-1H-imidazol-1-yl) propyl]-2-oxazolidinone; mp 89°-91° C. , 13, 565 (1955), was added The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 9 of 2-nitroimidazole (53 mmol) and 7.32 g of K2CO3 was heated at 60° C. for 0.5 hours. Then 8.6 g (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955)) was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone; mp 89°-91° C. The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated

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

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

Procedure: To a mechanically stirred, room temperature suspension of NaH (0.305 mole, hexane washed) in 50 mL of DMF under N2, was added 2-oxazolidinone (0.287 mole) portion wise. After stirring the resulting gelatinous mixture overnight, 1,3-dichloropropane (0.643 mole) was added and the mixture stirred 4 days at room temperature. The volatiles were then removed in vacuo and the resulting white residue taken up in CH2Cl2 and washed with H2O and brine, and dried over MgSO4. After filtration, the material was passed through a short column (SiO2 : EtOAc/Hex) to give (XVI) as a clear oil in 95% yield: 1H NMR (CDCl3) δ4.22 (t, 2H, J=6.6 Hz), 3.47 (m, 4H), 3.24 (t, 2H, J=7.0 Hz), and 1.98 (p, 2H, J=6.5 Hz); 13C NMR (CDCl3) δ158.5, 61.8, 45.0, 42.0, 41.8, and 30.2. Anal. Calcd for C6H10ClNO2 : C, 44.05; H, 6.16; N, 8.56. Found: 41.17; H, 5.77; N, 8.26. was added the mixture stirred 4 days at room temperature The volatiles were then removed in vacuo washed with H2O and brine dried over MgSO4 After filtration

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-nitroimidazole (53 mmol) and 7.32 g of K2CO3 was heated at 60° C. for 0.5 hours. Then 8.6 g (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955)) was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone; mp 89°-91-° C. The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 % of 2-nitroimidazole (53 mmol) and 7.32 % of KzCO3 was heated at 60° C. for 0.5 hours. Then 8.6 % (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955)) was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-3-(2-nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone; mp 89°-91° C. The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 g of 2-nitroimidazole (53 mmol) and 7.32 g of K2CO3 was heated at 60° C. for 0.5 hours. Then 8.6 g (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955), was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-[3-(2-nitro-1H-imidazol-1-yl) propyl]-2-oxazolidinone; mp 89°-91° C. , 13, 565 (1955), was added The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 6 9 of 2-nitroimidazole (53 mmol) and 7.32 g of K2CO3 was heated at 60° C. for 0.5 hours. Then 8.6 g (53 mmol) of 3-(3-chloropropyl)-2-oxazolidinone (Ann. Pharm. Franc., 13, 565 (1955)) was added and stirring continued for 18 hours at 60° C. The mixture was then cooled and concentrated. The residue was partitioned between CHCl3 and water, the organic layer was dried and concentrated to give 10.4 g of a solid which was recrystallized from ethanol to provide 5.4 g (42%) of the desired product, 3-[3-(2-nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone; mp 89°-91° C. The mixture was then cooled concentrated The residue was partitioned between CHCl3 and water the organic layer was dried concentrated