2-Nitroimidazole → 3-[3-(2-Nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinone

HRID 1087457Notes

Reaction equation

HRID 1087457 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Cl[CH2:16][CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][O:21][C:20]1=[O:24]>>[N+:1]([C:4]1[N:5]([CH2:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][O:21][C:20]2=[O:24])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 133549643-(3-Chloropropyl)-2-oxazolidinone

Product 1

HCID 148966273-[3-(2-Nitro-1H-imidazol-1-yl)propyl]-2-oxazolidinoneYield 81.7%

Conditions

Temperature
60 °C

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.

Workup

  1. addition, 13, 565 (1955), was added
  2. temperatureThe mixture was then cooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between CHCl3 and water
  5. customthe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a9a4fd5bb017499c96adaf4736b71822
Source dataset
uspto-grants-1991_07
Patent number
US05036089

Reaction notes

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