Hydrogen Peroxide → HCID 58541889, compound

HRID 1966725Notes

Reaction equation

HRID 1966725 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]#[N:12])=[N:8][C:4]=2[CH:3]=1.[OH-:23].[NH4+].OO>CO>[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[N:6]([C:17]([CH3:18])([CH3:19])[CH3:20])[C:7]([C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[C:11]([NH2:12])=[O:23])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14923Ammonium HydroxideHCID 58542011HCID 58542011, compound

Product 1

HCID 58541889HCID 58541889, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a round bottom flask is added 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzonitrile (1800 mg, 5.08 mmol) in MeOH (40 mL), followed by the addition of ammonium hydroxide (20 mL) and hydrogen peroxide (10 mL) (30% in water). The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is concentrated in vacuo. The residue is diluted with EtOAc, washed with water then brine, dried under Na2SO4, filtered and concentrated. The residue is loaded onto a silica gel column. The column is eluted with 0-4% MeOH/CH2Cl2. The product fractions are collected and concentrated to afford 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzamide (1590 mg, 84%) as a light brown solid. LCMS (ESMS): m/z 372.46, 374.35 (M++1)

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. additionThe residue is diluted with EtOAc
  3. washwashed with water
  4. dry with materialbrine, dried under Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe column is eluted with 0-4% MeOH/CH2Cl2
  8. customThe product fractions are collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-70def71dad41472a8face902f5ba2d4a
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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