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

HRID 1031549Notes

Reaction equation

HRID 1031549 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 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.

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-46a76c961fe8485c96b6db25dcb27e8a
Source dataset
uspto-grants-1990_09
Patent number
US04954515

Reaction notes

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