Imidazole → 1-[4-(4-t-Butylphenyl)butan-4-onyl]imidazole

HRID 463280Notes

Reaction equation

HRID 463280 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:21])[CH2:17][CH2:18][CH2:19]Cl)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>CN(C)C=O>[C:6]([C:10]1[CH:11]=[CH:12][C:13]([C:16](=[O:21])[CH2:17][CH2:18][CH2:19][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:14][CH:15]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 795ImidazoleHCID 27236944'-tert-Butyl-4-chlorobutyrophenone

Product 1

HCID 202824961-[4-(4-t-Butylphenyl)butan-4-onyl]imidazoleYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. slurry of 8.24 g of imidazole in 15 ml. dry dimethylformamide was added 5.79 g of p-t-butyl-gamma-chlorobutyrophenone and the mixture was stirred overnight at room temperature, then for one day at 60° C. The above solution was poured into 400 ml. of water and extracted three times with ethyl acetate. The combined extracts were washed with water, dried over magnesium sulfate and the solvent evaporated to afford 5.25 g of 1-[4-(4-t-butylphenyl)butan-4-onyl]imidazole as a golden oil.

Workup

  1. customTo a 0° C.
  2. waitfor one day at 60° C
  3. additionThe above solution was poured into 400 ml
  4. extractionof water and extracted three times with ethyl acetate
  5. washThe combined extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-5474642cacfe4a3b81f6d870e9488a59
Source dataset
uspto-grants-1985_05
Patent number
US04518607

Reaction notes

Loading…