Ethyl bromoacetate → Ethyl (3-acetyl-4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

HRID 1270401Notes

Reaction equation

HRID 1270401 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:10]([N:13]1[C:17]2[C:18]([Br:22])=[CH:19][CH:20]=[CH:21][C:16]=2[NH:15][C:14]1=[O:23])(=[O:12])[CH3:11]>>[C:10]([N:13]1[C:17]2[C:18]([Br:22])=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:14]1=[O:23])(=[O:12])[CH3:11]

Participants

4

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 184493611-Acetyl-7-bromo-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 86607788Ethyl (3-acetyl-4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Procedure

Sodium hydride (353 mg of a 60% dispersion in mineral oil, 8.84 mmol) and ethyl bromoacetate (1.15 mL, 8.84 mmol) were added to a solution of 1-acetyl-7-bromo-1,3-dihydro-2H-benzimidazol-2-one from Step B (1.5 g, 5.89 mmol) in DMP (20 mL) at 0° C. After 4 h, the reaction mixture was quenched with brine and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2::EtOAc—100:0 to 80:20, to give the title compound. MS: m/z=343 (M+1).

Workup

  1. customthe reaction mixture was quenched with brine
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-6238911933994ab18f1506a67714ae1b
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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