Sodium hydride → HCID 71202496, compound

HRID 1844564Notes

Reaction equation

HRID 1844564 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:3]=[CH:2]1.[H-].[Na+].I[CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18]>CN(C)C=O>[CH3:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][N:1]1[CH:5]=[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 148248991-Iodo-3,3-dimethylbutaneHCID 178470744HCID 178470744, compound

Product 1

HCID 71202496HCID 71202496, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 1H-imidazol-4-ylacetate (3.74 g) obtained in Step 1 was dissolved in N,N-dimethylformamide (30 mL). To this solution, sodium hydride (63%, 1.02 g) and 1-iodo-3,3-dimethylbutane (5.66 g) were added under ice cooling. The mixture was stirred overnight at room temperature and then separated into aqueous and organic layers by the addition of ethyl acetate and a saturated aqueous solution of ammonium chloride. The obtained aqueous solution was washed with saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (eluting solvent: methylene chloride/methanol=95/5) to obtain the title compound (2.32 g).

Workup

  1. customseparated into aqueous and organic layers
  2. additionby the addition of ethyl acetate
  3. washThe obtained aqueous solution was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (eluting solvent: methylene chloride/methanol=95/5)

Sources & evidence

ORD record
ord-56544d8c716d4d2eabd78128b0749071
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

Loading…