Ammonia → 3-Propyl-4-bromo-5-aminobenzimidazole

HRID 2186075Notes

Reaction equation

HRID 2186075 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[C:10]([NH2:13])[CH:11]=[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[C:9]([Br:14])=[C:10]([NH2:13])[CH:11]=[CH:12][C:7]=2[N:6]=[CH:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 183798703-Propyl-5-aminobenzimidazoleHCID 21226129Dichloromethane methanol

Product 1

HCID 183798953-Propyl-4-bromo-5-aminobenzimidazoleYield 37%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-propyl-5-aminobenzimidazole (0.71 g, 4.3 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 0.40 g (1.6 mmol, 37%) 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-39c23a656863418798eaef0c973e4d76
Source dataset
uspto-grants-2002_06
Patent number
US06403626B1

Reaction notes

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