Water → HCID 117840630, compound

HRID 714886Notes

Reaction equation

HRID 714886 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].Br[C:12]([CH3:19])([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14].O>CN(C)C=O>[CH3:18][C:12]([N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]1)([CH3:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 178526856HCID 178526856, compound

Product 1

HCID 117840630HCID 117840630, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitro-1H-imidazole (10 g) in N,N-dimethylformamide (150 mL) was added sodium hydride (60% in mineral oil, 4.2 g) in an ice bath, and the mixture was stirred at the same temperature for 20 min. To the reaction mixture was added ethyl 2-bromo-2-methylpropanoate (20 mL) at the same temperature, and the mixture was stirred overnight at 50° C. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (12 g).

Workup

  1. stirringthe mixture was stirred overnight at 50° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e3966803f4434aea807282ecf491a941
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

Loading…