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

HRID 1087581Notes

Reaction equation

HRID 1087581 reaction equation
[N+:1]([C:4]1[NH:5][CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].Cl[CH2:10][CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][O:15][C:14]1=[O:18]>>[N+:1]([C:4]1[N:5]([CH2:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 107012-NitroimidazoleHCID 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 % 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.

Workup

  1. temperatureThe mixture was then cooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between CHCl3 and water
  4. customthe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9b89bb5ed584b4a9e43353b36035100
Source dataset
uspto-grants-1991_07
Patent number
US05036096

Reaction notes

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