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

HRID 442509Notes

Reaction equation

HRID 442509 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[CH:6]1[C:11]([C:12]([CH2:14][CH2:15][CH2:16]Cl)=[O:13])=[CH:10][CH:9]=[C:8]([Cl:18])[CH:7]=1>CN(C)C=O>[Cl:18][C:8]1[CH:7]=[CH:6][C:11]([C:12](=[O:13])[CH2:14][CH2:15][CH2:16][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 27237814,4'-Dichlorobutyrophenone

Product 1

HCID 190783351-[4-(4-Chlorophenyl)butan-4-onyl]imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. slurry of 10.5 g. of imidazole in 15 ml. dry dimethylformamide was added 6.5 g. of γ,p-dichlorobutyrophenone and the mixture was stirred overnight at room temperature then 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 1-[4-(4-chlorophenyl)butan-4-onyl]imidazole, which was used in the next step. This material may be further purified, if necessary, through the nitrate salt.

Workup

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

Sources & evidence

ORD record
ord-8638fe06652943ee8f370931966af829
Source dataset
uspto-grants-1977_08
Patent number
US04045568

Reaction notes

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