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

HRID 1643218Notes

Reaction equation

HRID 1643218 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 2h, the resulting mixture is stirred over 24h, 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), washed,with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent is evaporated
  4. customthe product is purified through flash chromatography

Sources & evidence

ORD record
ord-1104959ac9db496d983a8fb6de416e7d
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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