Imidazole → Acetophenone, 2-(1-imidazolyl)-4'-phenethyl-

HRID 1680649Notes

Reaction equation

HRID 1680649 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][CH:11]=1)=[O:9].O>CN(C)C=O>[N:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 30087272-Chloro-1-[4-(2-phenylethyl)phenyl]ethan-1-one

Product 1

HCID 52758Acetophenone, 2-(1-imidazolyl)-4'-phenethyl-Yield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing 3.4 g of imidazole in 5 ml of dimethylformamide, stirred at 0/+5° C., 2.58 g of 4-chloroacetyl-bibenzyl were slowly added. The reaction mixture was stirred for few minutes, then allowed to stand and then poured into water. The product thus formed was filtered off, purified by silica gel column chromatography (eluant: benzene/acetone) and then crystallized from ethyl acetate to give 2.24 g of the title compound melting at 134°-6° C. Yield 77%.

Workup

  1. additionwere slowly added
  2. customThe product thus formed
  3. filtrationwas filtered off
  4. custompurified by silica gel column chromatography (eluant: benzene/acetone)
  5. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e6e495a422b34154a5a1fc4db748d16f
Source dataset
uspto-grants-1981_06
Patent number
US04275071

Reaction notes

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