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

HRID 2299137Notes

Reaction equation

HRID 2299137 reaction equation
[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH2:17])=[CH:16][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]Br.N.CO.C(Cl)(Cl)Cl>CC(O)=O>[CH2:1]([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([NH2:17])=[C:16]([Br:18])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 10890581-Benzyl-1H-benzimidazol-5-amineHCID 21584188Chloroform methanol

Product 1

HCID 183798211-Benzyl-4-bromo-5-aminobenzimidazoleYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1-benzyl-5-aminobenzimidazole (1.0 g, 5.0 mmol) in 40 ml of AcOH was added solution of Br2 in AcOH until it produces a precipitate. The reaction mixture was concentrated in vacuo to provide a brown solid which was subjected to column chromatography (5% NH3 sat'd MeOH/CHCl3) to provide 0.90 g (2.5 mmol, 60%) of the product.

Workup

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

Sources & evidence

ORD record
ord-91ea8d2b6f9a4f428f25f241976b329c
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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