Ammonia → HCID 178419285, compound

HRID 2299155Notes

Reaction equation

HRID 2299155 reaction equation
[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[NH:13][CH2:14][CH2:15][N:16]=1.[Br:17]Br.N>CC(O)=O.[Hg](OC(C)=O)OC(C)=O>[Br:1][C:2]1[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[CH:5]=[C:4]([Br:17])[C:3]=1[NH:11][C:12]1[NH:13][CH2:14][CH2:15][N:16]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 178419417HCID 178419417, compound

Product 1

HCID 178419285HCID 178419285, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 16683746DiacetyloxymercuryCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-bromo-5-(2-imidazolin-2-ylamino)benzimidazole (0.2 g, 0.7 mmol) in 10 ml AcOH was added 200 mg of Hg(OAc)2 and few drops of Br2. Reaction mixture was concentrated in vacuo, yielding a dark oily residue, which was subjected to silica gel column chromatography (NH3 sat'd 30% MeOH/EtOAc) to provide 210 mg (0.58 mmol, 86%) of the desired product. The product obtained was converted to the fumarate salt and recrystallized from EtOH to afford 0.051 g (14%) of the product as a white solid.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. customyielding a dark oily residue, which

Sources & evidence

ORD record
ord-68462ae14d69447f9971f4f38e926739
Source dataset
uspto-grants-2002_12
Patent number
US06495583B1

Reaction notes

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