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

HRID 1270402Notes

Reaction equation

HRID 1270402 reaction equation
C([N:4]1[C:8]2[C:9]([Br:13])=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]1=[O:20])(=O)C.Cl>C(O)C>[Br:13][C:9]1[C:8]2[NH:4][C:5](=[O:20])[N:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:7]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86607788Ethyl (3-acetyl-4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Product 1

HCID 86607789Ethyl (4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl (3-acetyl-4-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate (500 mg, 1.47 mmol) was dissolved in ethanol (10 mL) and 6 M aqueous HCl (20 mL) and heated at reflux. After 2 h, the reaction was concentrated and redissolved in ethanol (10 mL). The mixture was treated with concentrated H2SO4 (0.5 mL) and heated at reflux. After 1 h, the cooled reaction mixture was partitioned between saturated aqueous NaHCO3 and CH2Cl2. The organic layer was dried over sodium sulfate, filtered, and concentrated to give the title compound. MS: m/z=301 (M+1).

Workup

  1. temperatureat reflux
  2. concentrationthe reaction was concentrated
  3. dissolutionredissolved in ethanol (10 mL)
  4. additionThe mixture was treated with concentrated H2SO4 (0.5 mL)
  5. temperatureheated
  6. temperatureat reflux
  7. waitAfter 1 h
  8. customthe cooled reaction mixture
  9. customwas partitioned between saturated aqueous NaHCO3 and CH2Cl2
  10. dry with materialThe organic layer was dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-1dc211cf644d45f0bda984925aa11377
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

Loading…