Water → HCID 22928248, compound

HRID 523104Notes

Reaction equation

HRID 523104 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.Br[CH2:10][CH2:11][O:12][CH3:13].O>CN(C=O)C>[CH3:13][O:12][CH2:11][CH2:10][N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl ether

Product 1

HCID 22928248HCID 22928248, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (60%, 620 mg) was added to a solution of 2-methyl-1H-imidazole (1.06 g, 12.95 mmol) in DMF (8 mL). After stirring for 15 minutes, 1-bromo-2-methoxyethane (2.16 g, 15.54 mmol) in DMF (1 mL) was added. The resulting solution was stirred at 80° C. under microwave irradiation for 60 minutes. Water (1 mL) was added and all solvents were removed by high vacuum. EtOAc was added to the residue, stirred for 15 minutes, filtered and concentrated in vacuo to afford the title compound as a colourless oil (604 mg, 33%) that was used directly in the next step.

Workup

  1. stirringThe resulting solution was stirred at 80° C. under microwave irradiation for 60 minutes
  2. customall solvents were removed by high vacuum
  3. additionEtOAc was added to the residue
  4. stirringstirred for 15 minutes
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25373dd7b7a043ca9fd6b423a33a4e4b
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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