Imidazole → 1-([1,1'-Biphenyl]-4-yl)-2-(1H-imidazol-1-yl)ethan-1-one

HRID 1389779Notes

Reaction equation

HRID 1389779 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:10]([C:11](=[O:14])[CH2:12]Br)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.O>CN(C)C=O>[N:17]1([CH2:12][C:11]([C:10]2[CH:15]=[CH:16][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][CH:9]=2)=[O:14])[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 672821-(1,1'-Biphenyl)-4-yl-2-bromoethanone

Product 1

HCID 517091-([1,1'-Biphenyl]-4-yl)-2-(1H-imidazol-1-yl)ethan-1-oneYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

39 g (0.14 mol) of 4-phenylphenacyl bromide are introduced in portions into a solution of 48.2 g (0.7 mol) of imidazole in 140 ml of dimethylformamide, whilst cooling. The mixture is allowed to subsequently react for 15 hours and the solution is poured into water. The crystal mass which has separated out is recrystallised from ethanol. 24 g (65% of theory) of 4-biphenylyl imidazol-1-yl-methyl ketone of melting point 198° C. are obtained.

Workup

  1. temperaturewhilst cooling
  2. customto subsequently react for 15 hours
  3. customThe crystal mass which has separated out
  4. customis recrystallised from ethanol

Sources & evidence

ORD record
ord-30f59f05e9d541cc8c788b4ef056d9b6
Source dataset
uspto-grants-1981_01
Patent number
US04246274

Reaction notes

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