1-Bromo-2-Chloroethane → HCID 89586388, compound

HRID 333753Notes

Reaction equation

HRID 333753 reaction equation
Cl.[NH:2]1[CH:6]=[CH:5][N:4]2[CH:7]=[CH:8][N:9]=[C:3]12.[H-].[Na+].Br[CH2:13][CH2:14][Cl:15]>CN(C=O)C>[Cl:15][CH2:14][CH2:13][N:2]1[CH:6]=[CH:5][N:4]2[CH:7]=[CH:8][N:9]=[C:3]12

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydrideHCID 89586484106538-25-4

Product 1

HCID 89586388HCID 89586388, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an argon atmosphere, to a solution of 1H-imidazo[1,2-a]imidazole.hydrochloride (85 mg) in DMF (3 mL) was added 60% sodium hydride (52.1 mg), and the mixture was stirred under ice-cooling for 1 hr. Then, a solution of 1-bromo-2-chloroethane (170 mg) in DMF (0.5 mL) was added, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (38 mg).

Workup

  1. temperaturecooling for 1 hr
  2. stirringthe mixture was stirred at room temperature for 18 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-e292f781808e4385bc922bd22db80efd
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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