Sodium borohydride → HCID 11372470, compound

HRID 644538Notes

Reaction equation

HRID 644538 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[N:18][C:14]=3[CH:13]=[C:12]([C:25]([F:28])([F:27])[F:26])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[N:18][C:14]=3[CH:13]=[C:12]([C:25]([F:28])([F:27])[F:26])[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 114289357-(3-Acetylphenyl)-1-phenyl-5-trifluoromethylbenzimidazole

Product 1

HCID 11372470HCID 11372470, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 7-(3-acetylphenyl)-1-phenyl-5-trifluoromethylbenzimidazole (0.95 g, 2.5 mmol) in ethanol (10 ml) was added sodium borohydride (0.1 g, 2.6 mmol) and the resultant mixture was stirred at 60° C. for 20 min. The cooled reaction mixture was concentrated under reduced pressure and the concentrate was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate and concentrated to a small volume (1-2 ml) under reduced pressure. The title product precipitated upon addition of ligroin to the concentrate (0.65 g, 68%) m/z, 383.1 (M+H)+.

Workup

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated under reduced pressure
  3. customthe concentrate was partitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated to a small volume (1-2 ml) under reduced pressure
  6. customThe title product precipitated upon addition of ligroin to the
  7. concentrationconcentrate (0.65 g, 68%) m/z, 383.1 (M+H)+

Sources & evidence

ORD record
ord-239daf1ea2b144a9995990f6769d72fe
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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