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

HRID 1938602Notes

Reaction equation

HRID 1938602 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 moles, 6.8 g) was dissolved in 200 ml DMF. Sodium hydride (47.5 moles, 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-9bd822178c864d109ee89194f52ec93a
Source dataset
uspto-grants-1997_12
Patent number
US05693633

Reaction notes

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