Azobisisobutyronitrile → HCID 19841102, compound

HRID 1638563Notes

Reaction equation

HRID 1638563 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][C:24]([OH:26])=[O:25])=[CH:13][CH:12]=2)[C:8]2[CH:27]=[C:28]([CH:31]=[O:32])[CH:29]=[CH:30][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[Br:33]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:33][CH:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][C:24]([OH:26])=[O:25])=[CH:15][CH:16]=2)[C:8]2[CH:27]=[C:28]([CH:31]=[O:32])[CH:29]=[CH:30][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19841104HCID 19841104, compound

Product 1

HCID 19841102HCID 19841102, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a mixture 0.55 g of 2-butyl-1-[(2'-carboxymethylbiphenyl-4-yl)methyl]benzimidazole-6-carboxaldehyde in 30 mL of carbon tetrachloride was added 0.23 g of N-bromosuccinimide and a catalytic amount of azobisisobutyronitrile. The reaction was stirred at room temperature until the reaction went to completion and then concentrated to dryness. The residue was partitioned between ethyl acetate and water. The organic phase was washed with water, dried and concentrated. Flash column chromatography (silica gel; 1:1 hexane/ethyl acetate to 1:3 hexane/ethyl acetate) afforded 0.45 g of the product as a thick clear oil.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2ba6901a340947cf80c180fe9aa56db6
Source dataset
uspto-grants-1989_11
Patent number
US04880804

Reaction notes

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