Ethyl Bromide → HCID 22459862, compound

HRID 2185135Notes

Reaction equation

HRID 2185135 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-5a26dada124b49ce9bea4109e55b9af3
Source dataset
uspto-grants-2002_06
Patent number
US06399782B1

Reaction notes

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