Hydroxylamine → HCID 178448432, compound

HRID 1966762Notes

Reaction equation

HRID 1966762 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.[NH2:23][OH:24]>CCO>[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]([NH:23][OH:24])=[NH:12])=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58542011HCID 58542011, compound

Product 1

HCID 178448432HCID 178448432, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-benzonitrile (765 mg, 2.16 mmol) in EtOH (15 mL) is added hydroxylamine 50% aqueous solution (2.85 mL, 43.19 mmol) at room temperature. The solution is heated to 80° C. for 2 hours. The reaction mixture is cooled to room temperature and the ethanol removed in vacuo. Water (30 mL) is added to the reaction mixture and the resultant precipitate is filtered and washed with 10% EtOAc/heptane (10 mL) to afford 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-N-hydroxy-benzamidine (716 mg, 81%).

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. customthe ethanol removed in vacuo
  3. additionWater (30 mL) is added to the reaction mixture
  4. filtrationthe resultant precipitate is filtered
  5. washwashed with 10% EtOAc/heptane (10 mL)

Sources & evidence

ORD record
ord-8631b78c487a43aaa55115e2ec4e8469
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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