Azobisisobutyronitrile → HCID 22285068, compound

HRID 1061872Notes

Reaction equation

HRID 1061872 reaction equation
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[CH:36]=[C:35]([C:40]([O:42][CH3:43])=[O:41])[C:34]([CH3:44])=[CH:33]2)([C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1)[CH:3]([CH3:5])[CH3:4].[Br:45]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:45][CH2:44][C:34]1[C:35]([C:40]([O:42][CH3:43])=[O:41])=[CH:36][C:37]2[C:32]([CH:33]=1)=[CH:31][C:30]([C:2]([OH:1])([C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:10]=1)[CH:3]([CH3:5])[CH3:4])=[CH:39][CH:38]=2

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 22285057HCID 22285057, compound

Product 1

HCID 22285068HCID 22285068, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-3-methyl-2-naphthoate (5.93 g) was suspended in carbon tetrachloride (150 ml) and N-bromosuccinimide (2.01 g) and 2,2′-azobisisobutyronitrile (0.17 g) were added. The reaction mixture was heated under reflux for 4 hrs. and the solvent was concentrated. The residue was diluted with saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give a crude title compound (6.70 g) as a brown amorphous solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationand the solvent was concentrated
  4. additionThe residue was diluted with saturated aqueous sodium hydrogen carbonate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ce2a0861c6e445eb8c7b4d7b80054ae4
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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