N-bromobutanimide → HCID 22285043, compound

HRID 1061876Notes

Reaction equation

HRID 1061876 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[N:15]=[CH:16][N:17]([C:19]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH:18]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:38]([O:40][CH3:41])=[O:39].[Br:42]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:42][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([C:14]3[N:15]=[CH:16][N:17]([C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH:18]=3)=[O:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:38]([O:40][CH3:41])=[O:39]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22285044HCID 22285044, compound

Product 1

HCID 22285043HCID 22285043, compoundYield 108.2%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 1-methyl-6-[(1-trityl-1H-imidazol-4-yl)carbonyl]-2-naphthoate (20.7 g) was suspended in carbon tetrachloride (400 mL) and N-bromosuccinimide (7.5 g) and 2,2′-azobisisobutyronitrile (0.58 g) were added. The reaction mixture was heated under reflux for 5 hrs. and concentrated. The residue was diluted with saturated aqueous sodium hydrogen carbonate and extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give a crude title compound (25.7 g) as a brown amorphous solid.

Workup

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

Sources & evidence

ORD record
ord-c2062ab7c02b4ed59f94ff8544c8ab76
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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