Ammonia → 1-Propyl-4-bromo-5-aminobenzimidazole

HRID 2299127Notes

Reaction equation

HRID 2299127 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[CH:12][C:7]=2[N:6]=[CH:5]1)[CH2:2][CH3:3].[Br:14]Br.N.CO.C(Cl)Cl>CC(O)=O>[CH2:1]([N:4]1[C:8]2[CH:9]=[CH:10][C:11]([NH2:13])=[C:12]([Br:14])[C:7]=2[N:6]=[CH:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 183798881-Propyl-1H-benzoimidazol-5-ylamineHCID 21226129Dichloromethane methanol

Product 1

HCID 183799021-Propyl-4-bromo-5-aminobenzimidazoleYield 48%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1-propyl-5-aminobenzimidazole (1.2 g, 7.1 mmol) in 10 ml of AcOH was added solution of Br2 in AcOH until it produces a precipitation. The reaction mixture was concentrated in vacuo to provide a brown solid which was subjected to column chromatography (5% NH3 sat'd MeOH/CH2Cl2) to provide 0.83 g (3.4 mmol, 48%) of the product.

Workup

  1. customproduces
  2. customa precipitation
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customto provide a brown solid which

Sources & evidence

ORD record
ord-bde3e74aa5b2434ca12bb213f2e44d4b
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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