Azobisisobutyronitrile → HCID 68771618, compound

HRID 1398916Notes

Reaction equation

HRID 1398916 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6]1=[O:18].N(C(C)(C)C#N)=NC(C)(C)C#N.[Br:31]N1C(=O)CCC1=O>C(OCC)(=O)C>[Br:31][C:13]1[C:8]2[NH:7][C:6](=[O:18])[N:5]([CH2:4][CH2:3][CH2:2][Cl:1])[C:9]=2[C:10]([C:14]([O:16][CH3:17])=[O:15])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68763070HCID 68763070, compound

Product 1

HCID 68771618HCID 68771618, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of methyl 3-(3-chloropropyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate (5.00 g, 18.6 mmol) and 2,2′-azobis(isobutyronitrile) (3.06 g, 18.6 mmol) in ethyl acetate (90 mL) was stirred at 70° C. for 40 min. N-Bromosuccinimide (3.31 g, 18.6 mmol) was added portionwise to the reaction mixture and the resultant mixture was stirred 70° C. for 5 h. The reaction mixture was washed with aqueous saturated sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture to give the title compound as a colorless solid (490 mg, 1.41 mmol, 7.6%).

Workup

  1. washThe reaction mixture was washed with aqueous saturated sodium hydrogen carbonate and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-e33dfbf946a54a388f3ef3fae5ab65e4
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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