Azobisisobutyronitrile → Methyl 1-bromomethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthoate

HRID 1061871Notes

Reaction equation

HRID 1061871 reaction equation
[OH:1][C:2]([C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[C:36]([CH3:40])=[C:35]([C:41]([O:43][CH3:44])=[O:42])[CH:34]=[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][CH2:40][C:36]1[C:37]2[C:32](=[CH:31][C:30]([C:2]([OH:1])([C:6]3[N:7]=[CH:8][N:9]([C:11]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:10]=3)[CH:3]([CH3:5])[CH3:4])=[CH:39][CH:38]=2)[CH:33]=[CH:34][C:35]=1[C:41]([O:43][CH3:44])=[O:42]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 22285053Methyl 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-1-methyl-2-naphthoate

Product 1

HCID 22285061Methyl 1-bromomethyl-6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]-2-naphthoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Methyl 6-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl)-1-methyl-2-naphthoate (34.61 g) was suspended in carbon tetrachloride (0.8 L) and N-bromosuccinimide (12.28 g) and 2,2′-azobisisobutyronitrile (0.99 g) were added. The reaction mixture was heated under reflux for 21 hrs., and the solvent was evaporated. The residue was diluted with saturated aqueous sodium hydrogen carbonate and extracted twice with ethyl acetate-THF (1:1). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography (carrier;silica gel, developing solvent; ethyl acetate) to give a mixture of the title compound and the starting material (title compound:starting material=about 7:1, 23.10 g) as brown crystals.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 21 hrs
  3. custom, and the solvent was evaporated
  4. additionThe residue was diluted with saturated aqueous sodium hydrogen carbonate
  5. extractionextracted twice with ethyl acetate-THF (1:1)
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customThe obtained residue was purified by column chromatography (carrier;silica gel, developing solvent; ethyl acetate)
  10. customto give

Sources & evidence

ORD record
ord-2aa38b4b474f4416a3bb4aed0b826959
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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