Hydrochloric Acid → HCID 59208466, compound

HRID 2243070Notes

Reaction equation

HRID 2243070 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12](=[O:14])[CH3:13].Cl.C([O-])(O)=O.[Na+].[CH3:21][O:22][C:23](=O)[O:24]C>>[CH3:3][O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12](=[O:14])[CH2:13][C:23]([O:22][CH3:21])=[O:24]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 59208500HCID 59208500, compound2×

Product 1

HCID 59208466HCID 59208466, compound

Conditions

Temperature
90 °C

Procedure

NaH (7.84 g, 196 mmol of a 60% dispersion in oil) was added portionwise to a solution of 6.18 g (Intermediate 57, 34.5 mmol) of 1-[1-(2-methoxyethyl)-1H-imidazol-2-yl]ethanone in 100 ml dimethylcarbonate. The mixture was heated to 90° C. for 2 hour forming a thick slurry. After cooling to room temperature, the mixture was slowly transferred to 1N HCl over ice. The mixture was brought to about pH 7 with NaHCO3, then saturated with NaCl and extracted 4 times with EtOAc. The EtOAc was dried over MgSO4, then concentrated to give an oil that was chromatographed on silica gel (100% DCM followed by gradient elution to 50% EtOAc in DCM) to yield the title compound. MS (ES) (M+H)+: 227 for C10H14N2O4; NMR: 3.18 (s, 3H), 3.61 (m, 5H), 4.07 (s, 2H), 4.52 (m, 2H), 7.24 (s, 1H), 7.61 (s, 1H).

Workup

  1. customforming a thick slurry
  2. temperatureAfter cooling to room temperature
  3. extractionsaturated with NaCl and extracted 4 times with EtOAc
  4. dry with materialThe EtOAc was dried over MgSO4
  5. concentrationconcentrated
  6. customto give an oil that
  7. customwas chromatographed on silica gel (100% DCM followed by gradient elution to 50% EtOAc in DCM)

Sources & evidence

ORD record
ord-81bd22be8b7d4584bb7036c6f6280958
Source dataset
uspto-grants-2010_03
Patent number
US07674801B2

Reaction notes

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