Butyl bromide → 3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazole

HRID 457386Notes

Reaction equation

HRID 457386 reaction equation
[OH-].[K+].[C:3]1([C:9]2[NH:10][CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:23][CH2:24][CH2:25][CH3:26]>CS(C)=O>[CH2:23]([N:10]1[CH:11]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[N:13]=[C:9]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14797Potassium HydroxideHCID 178488774HCID 178488774, compound

Product 1

HCID 588180333-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Potassium hydroxide (4.36, 76 mmol, 1.3 eq.) is suspended in 40 ml of anhydrous DMSO, to the suspension is added a solution 2-phenyl-4-(4-methoxyphenyl)imidazole (15.02, 60 mmol) and bromobutane (8.63 g, 63 mmol, 1.05 eq.) in 80 ml of DMSO at room temperature over 2 h, the resulting mixture is stirred over 24 h, and then poured into 400 ml of ice-water, extracted with ethyl acetate (100 ml×4), washed with water and brine, dried over anhydrous sodium sulfate. The solvent is evaporated and the product is purified through flash chromatography to give 16.73 g of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazole. MS (+VE) m/z 307 (M+1).

Workup

  1. extractionextracted with ethyl acetate (100 ml×4)
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent is evaporated
  5. customthe product is purified through flash chromatography

Sources & evidence

ORD record
ord-4c7661d1732c4dd3bcd061eb844213b5
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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