Benzaldehyde → 7-(N-benzylideneamino)-1-phenyl-5-trifluoromethylbenzimidazole

HRID 644504Notes

Reaction equation

HRID 644504 reaction equation
[NH2:1][C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1.[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:21](=[N:1][C:2]1[C:7]2[N:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[CH:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 6101p-Toluenesulfonic acidHCID 113003637-Amino-1-phenyl-5-trifluoromethylbenzimidazole

Product 1

HCID 114172137-(N-benzylideneamino)-1-phenyl-5-trifluoromethylbenzimidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 7-amino-1-phenyl-5-trifluoromethylbenzimidazole (0.50 g, 1.81 mmol) in anhydrous toluene (10 ml) was added benzaldehyde, p-toluenesulphonic acid (10 mg) and molecular sieves. The resultant mixture was stirred at reflux for 1.5 hours. The molecular sieves were removed by filtration and the filtrate was concentrated under reduced pressure. The concentrate was partitioned between aqueous sodium carbonate (2M) and ethyl acetate. The organic phase was dried and concentrated, and the concentrate was eluted through silica gel with a mixture of ethyl acetate and ligroin (1:1 v/v). Removal of solvent from the eluate left the desired product as a yellow solid (0.37 g, 56%) m/z, 366.1 (M+H)+.

Workup

  1. temperatureat reflux for 1.5 hours
  2. customThe molecular sieves were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe concentrate was partitioned between aqueous sodium carbonate (2M) and ethyl acetate
  5. customThe organic phase was dried
  6. concentrationconcentrated
  7. washthe concentrate was eluted through silica gel with a mixture of ethyl acetate and ligroin (1:1 v/v)
  8. customRemoval of solvent from the eluate
  9. waitleft the desired product as a yellow solid (0.37 g, 56%) m/z, 366.1 (M+H)+

Sources & evidence

ORD record
ord-5c9a39aaa8d74e3c91b89fbc8acc70aa
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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