Hydrogen Bromide → HCID 178493431, compound

HRID 620837Notes

Reaction equation

HRID 620837 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[NH:12][C:13]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[C:14]([CH3:16])[N:15]=1.[BrH:23].[OH-].[Na+]>C(O)(=O)C.Br.[NH+]1C=CC=CC=1>[Br:23][C:6]1[C:7]([O:9][CH3:10])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:11]2[NH:12][C:13]([C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[C:14]([CH3:16])[N:15]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 178488939HCID 178488939, compound

Product 1

HCID 178493431HCID 178493431, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 21226041Pyridinium hydrobromideSolvent

Procedure

To a solution of 2-(2,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (1.0 g) in acetic acid (10 ml) were added a solution of hydrogen bromide in acetic acid (28%, 0.2 ml) and pyridinium hydrobromide perbromide (1.49 g), and was stirred at ambient temperature for 19 hours. Then the mixture was poured into ice-water (100 ml), adjusted to pH 4.8 with 8N sodium hydroxide, and extracted with chloroform. The organic layer was washed by aqueous sodium bicarbonate and evaporated, and the residue was triturated in diisopropyl ether to give 2-(5-bromo-2,4-dimethoxyphenyl)-4-methyl-5-(3-pyridyl)imidazole (0.92 g).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed by aqueous sodium bicarbonate
  3. customevaporated
  4. customthe residue was triturated in diisopropyl ether

Sources & evidence

ORD record
ord-ffb839ab8a0142fd916ab1eb64e0ca9a
Source dataset
uspto-grants-1989_04
Patent number
US04822805

Reaction notes

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