Ethyl Bromide → HCID 22459862, compound

HRID 1872514Notes

Reaction equation

HRID 1872514 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].Br[CH2:17][CH3:18]>CN(C)C=O>[CH2:17]([N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:4]=2[N:3]=[C:2]1[CH3:1])[CH3:18]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 178432173HCID 178432173, compound

Product 1

HCID 22459862HCID 22459862, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 0.47 g (2.65 mmol) 2-methyl-4-nitrobenzimidazole, and 0.12 g (2.92 mmol) of sodium hydride in 10 mL of dry dimethylformamide was added 0.218 mL (2.92 mmol) bromoethane. The mixture was heated overnight at 65° C. The mixture was cooled to room temperature and the solvents were removed under reduced pressure. The resultant syrup was partitioned between water and ethyl acetate. The organic phase was evaporated to dryness and the syrup chromatographed on silica to yield 0.31 g (1.51 mmol, 52%) of a yellow syrup.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvents were removed under reduced pressure
  3. customThe resultant syrup was partitioned between water and ethyl acetate
  4. customThe organic phase was evaporated to dryness
  5. customthe syrup chromatographed on silica

Sources & evidence

ORD record
ord-869958eab56e475d893b2a47cd00c2a2
Source dataset
uspto-grants-2000_08
Patent number
US06110903

Reaction notes

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