Hydrogen Bromide → HCID 68771334, compound

HRID 1398798Notes

Reaction equation

HRID 1398798 reaction equation
N[C:2]1[C:7]2[N:8]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.N([O-])=O.[Na+].C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[K+].[K+].[BrH:35]>C(O)(=O)C.S(=O)(=O)(O)O.[Cu]Br>[Br:35][C:2]1[C:7]2[N:8]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:9](=[O:11])[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 68773936HCID 68773936, compound

Product 1

HCID 68771334HCID 68771334, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 176Acetic AcidSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 4-(7-amino-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)butanoate (23.0 g, 87.3 mmol) in acetic acid (250 mL) was added dropwise sodium nitrite (6.32 g, 91.7 mmol) in conc. sulfuric acid (80 mL) at 0° C., and the mixture was stirred at 0° C. for 20 min. The mixture was added dropwise to a solution of copper(I) bromide (50.1 g, 350 mmol) in conc. hydrobromic acid (150 mL) at 0° C., and the mixture was stirred at room temperature for 2 hr. The mixture was poured into aqueous sodium hydrogen carbonate, neutralized with potassium carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with diisopropyl ether, recrystallized from ethyl acetate to give the title compound as a pale yellow crystal (5.79 g, 17.7 mmol, 20%).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with diisopropyl ether
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-443db7163b27458da65b86576f295e50
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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