Sodium hydride → Ethyl 2-(4-nitro-1H-imidazole-1-yl)octanoate

HRID 1609758Notes

Reaction equation

HRID 1609758 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]([O:15][CH2:16][CH3:17])=[O:14]>CN(C=O)C>[N+:1]([C:4]1[N:5]=[CH:6][N:7]([CH:12]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:8]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 95580Ethyl 2-bromooctanoateHCID 178526856HCID 178526856, compound

Product 1

HCID 10062368Ethyl 2-(4-nitro-1H-imidazole-1-yl)octanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitroimidazole (0.29 moles, 32.9 g in 30 ml DMF was treated portionwise with sodium hydride (0.29 moles, 11.6 g. 60% in mineral oil) and stirred for 45 minutes. Ethyl 2-bromooctanoate (0.29 moles, 73.1 g) was added dropwise over 1 hour. The reaction was stirred overnight at room temperature, poured onto ice water, and extracted with ethyl acetate. The organic phase was washed with brine, dried and concentrated to yield 91 g of ethyl 2-(4-nitro-1H-imidazol-1-yl)octanoate. (MS)

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. additionpoured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-538dbcb731df4dcea52c87eba551061e
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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