Sodium Hydroxide → HCID 67151219, compound

HRID 1892605Notes

Reaction equation

HRID 1892605 reaction equation
[Br:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[C:4]([C:12]([O:14]C)=[O:13])[CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[C:7]2[NH:8][C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[C:4]([C:12]([OH:14])=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 671513581H-Benzimidazole-5-carboxylic acid, 7-bromo-2,3-dihydro-2-oxo-, methyl ester

Product 1

HCID 67151219HCID 67151219, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 7-bromo-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-5-carboxylate (238 mg, 0.878 mmol) and 2 N aqueous sodium hydroxide (1.50 mL, 3.0 mmol) were combined in methanol (5 mL) and heated to 50° C. for 90 minutes. The reaction solution was concentrated to remove the methanol. To the reaction residue was added ethyl acetate (5 mL). The resultant solution was acidified with 1N aqueous hydrochloric acid (1.5 mL) to give a final pH of 4. A precipitate formed which was filtered and dried under vacuum to give the title compound (226 mg, 100%) as a solid. 1H NMR (400 MHz, CD3OD) δ ppm 7.89 (d, J=1.37 Hz, 1H) 7.65 (d, J=1.37 Hz, 1H).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customto remove the methanol
  3. additionTo the reaction residue was added ethyl acetate (5 mL)
  4. customto give a final pH of 4
  5. customA precipitate formed which
  6. filtrationwas filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-49fa78807a634b1da2f8f1834000dee8
Source dataset
uspto-grants-2013_08
Patent number
US08507681B2

Reaction notes

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