Benzyl Bromide → HCID 12832388, compound

HRID 370775Notes

Reaction equation

HRID 370775 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][NH:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1.[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.C(OCC)(=O)C>[CH3:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]2[N:14]=[CH:13][N:12]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:11]=2[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 14100143HCID 14100143, compound

Product 1

HCID 12832388HCID 12832388, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Incremental portions of 1.8 g of sodium hydride (50% strength in white oil) is added to a solution of 10.5 g of 4,5-bis(4-methoxyphenyl)imidazole in 50 ml of absolute dimethylformamide. The mixture is agitated for 30 minutes and then 6.75 g of benzyl bromide in 50 ml of dimethylformamide is added dropwise thereto. After 30 minutes, the mixture is poured on ice water, the product is taken up in ethyl acetate, the organic solution dried over sodium sulfate and concentrated to dryness under vacuum. The residue is recrystallized from ethanol, thus obtaining 13.89 g of 4,5-bis(4-methoxyphenyl)-1-benzylimidazole, mp 165°-167°.

Workup

  1. waitAfter 30 minutes
  2. additionthe mixture is poured on ice water
  3. dry with materialthe organic solution dried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-9bd43acde85446f2a75d54bea2fc8025
Source dataset
uspto-grants-1985_07
Patent number
US04528298

Reaction notes

Loading…