Cesium carbonate → 1-neopentyl-4-(4-nitrophenyl)-1H-imidazole

HRID 873589Notes

Reaction equation

HRID 873589 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24]>CN(C)C=O.C(OCC)(=O)C>[CH2:22]([N:13]1[CH:14]=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[N:11]=[CH:12]1)[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 124151-Bromo-2,2-dimethylpropaneHCID 178418805HCID 178418805, compound

Product 1

HCID 867020761-neopentyl-4-(4-nitrophenyl)-1H-imidazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-nitrophenyl)-1H-imidazole (0.500 g, 2.64 mmol) in N,N-dimethylformamide (10 ml) was added cesium carbonate (1.292 g, 3.96 mmol) followed by 1-bromo-2,2-dimethylpropane (0.366 ml, 2.91 mmol). After heating at 85° overnight, the reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, filtered and concentrated. Normal phase chromatography provided the title compound.

Workup

  1. temperatureAfter heating at 85° overnight
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a67a282fd81477783e1d0d70467bbff
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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