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

HRID 1031548Notes

Reaction equation

HRID 1031548 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][N:18]1[CH2:22][CH2:21][O:20][C:19]1=[O:23]>CN(C=O)C>[N+:1]([C:4]1[N:5]([CH2:16][CH2:17][N:18]2[CH2:22][CH2:21][O:20][C:19]2=[O:23])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 107012-NitroimidazoleHCID 11430Potassium CarbonateHCID 756333-(2-Chloroethyl)-1,3-oxazolidin-2-one

Product 1

HCID 148966263-[2-(2-Nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinoneYield 35.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5 g (44 mmol) of 2-nitroimidazole and 6.1 g of K2CO3 in 50 ml of DMF was heated at 60° C. for 0.5 hours; then 6.61 g (44 mmol) of 3-(2-chloroethyl)-2-oxazolidinone 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 a solid. The solid was crystallized from ethanol to give 3.5 g (35%) of the desired product, 3-[2-(2-nitro-1H-imidazol-1-yl)ethyl]-2-oxazolidinone; mp 103°-104° C.

Workup

  1. customat 60° C
  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 to a solid
  7. customThe solid was crystallized from ethanol

Sources & evidence

ORD record
ord-37d2bd05c09c488b95565a6bd675550c
Source dataset
uspto-grants-1990_09
Patent number
US04954515

Reaction notes

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