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

HRID 866252Notes

Reaction equation

HRID 866252 reaction equation
[N+:1]([C:4]1[C:12]2[NH:11][CH:10]=[N:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Br[CH:16]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CN(C=O)C>[N+:1]([C:4]1[C:12]2[N:11]=[CH:10][N:9]([CH:16]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 95580Ethyl 2-bromooctanoateHCID 178526550HCID 178526550, compound

Product 1

HCID 21468887Ethyl 2-(4-nitro-1H-benzimidazol-1-yl)octanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitrobenzimidazole (41.7 mmoles, 6.8 g) was dissolved in 200 ml DMF. Sodium hydride (47.5 mmoles, 1.9 g of 60% in mineral oil) was added portionwise. The reaction was stirred for 30 minutes. Ethyl 2-bromooctanoate was added. The reaction stirred at room temperature for 3 hours and concentrated. Ethyl acetate and water were added; and the layers separated. The organic layer was washed with brine, dried over sodium sulfate and concentrated. The intermediate was purified by HPLC over silica gel eluted with a gradient of 0-50% ethyl acetate in hexane. The reaction yielded 10.3 g of ethyl 2-(4-nitro-1H-benzimidazol-1-yl)octanoate. (MS)

Workup

  1. stirringThe reaction stirred at room temperature for 3 hours
  2. concentrationconcentrated
  3. additionEthyl acetate and water were added
  4. customand the layers separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customThe intermediate was purified by HPLC over silica gel
  9. washeluted with a gradient of 0-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d2cac922bfe247e3b4491da7ac616d7b
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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