Butyl bromide → 1-Butyl-4-dimethoxymethyl-2-phenyl-1H-imidazole

HRID 457395Notes

Reaction equation

HRID 457395 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[N:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:7][CH:8]=1.[CH2:17](Br)[CH2:18][CH2:19][CH3:20].[OH-].[K+]>CS(C)=O.CCOCC>[CH2:17]([N:7]1[CH:8]=[C:4]([CH:3]([O:2][CH3:1])[O:15][CH3:16])[N:5]=[C:6]1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 1784995604-Dimethoxymethyl-2-phenyl-1H-imidazole

Product 1

HCID 184377881-Butyl-4-dimethoxymethyl-2-phenyl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4-dimethoxymethyl-2-phenyl-1H-imidazole 208 (2.18 g, 10 mmol) and n-butyl bromide (2.74 g, 20 mmol) in anhydrous DMSO (15 mL) is added to a suspension of powdered potassium hydroxide (0.96 mg, 15 mmol) in DMSO (20 mL) at room temperature over 3 h. The mixture is then stirred at rt for 16 h. The mixture is diluted with ether and washed with water (three times), brine, and dried over anhydrous sodium sulfate. Removal of the solvent and purification of the residue affords the desired product. Yield: 2.5 g; LC-MS (MH+): 275.

Workup

  1. washwashed with water (three times), brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customRemoval of the solvent and purification of the residue

Sources & evidence

ORD record
ord-1e41df7030434fe9adac9bc5e2f614bb
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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