Hydrazine → HCID 58542054, compound

HRID 1966730Notes

Reaction equation

HRID 1966730 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]([C:9]3[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=3[C:11](/[N:13]=[C:14](/[N:16](C)C)\[CH3:15])=O)=[N:8][C:4]=2[CH:3]=1.[NH2:29]N>C(O)(=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:7]([C:9]3[CH:22]=[CH:21][CH:20]=[CH:19][C:10]=3[C:11]3[N:13]=[C:14]([CH3:15])[NH:16][N:29]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 178464745HCID 178464745, compound

Product 1

HCID 58542054HCID 58542054, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask is added 2-(5-bromo-1-tert-butyl-1H-benzimidazol-2-yl)-N-[1-dimethylamino-eth-(E)-ylidene]-benzamide (237 mg, 0.537 mmol) in glacial acetic acid (3 mL), followed by the addition of hydrazine (35% wt solution in water) (2 mL). The reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is diluted with EtOAc, is washed with sat. NaHCO3, brine, dried under anhy. Na2SO4, filtered and concentrated. The residue is loaded to a silica gel column. The column is eluted with 0-3% 2M NH3 in MeOH/CH2Cl2. The product fractions are collected and concentrated to afford 5-bromo-1-tert-butyl-2-[2-(5-methyl-1H-1,2,4-triazol-3-yl)-phenyl]-1H-benzimidazole (78 mg, 35%) as a light brown solid. LCMS (ESMS): m/z 410.68, 412.71 (M++1)

Workup

  1. washis washed with sat. NaHCO3, brine
  2. customdried under anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated
  5. washThe column is eluted with 0-3% 2M NH3 in MeOH/CH2Cl2
  6. customThe product fractions are collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f3b214e2d07e4667a9611265320d083b
Source dataset
uspto-grants-2013_04
Patent number
US08420655B2

Reaction notes

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