Pyridine → Phenyl imidazole biphenyl

HRID 22044Notes

Reaction equation

HRID 22044 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([C:19]2[N:20]=[C:21](O)NC=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[N:25]1C=CC=C[CH:26]=1.S(Cl)(Cl)=O>C(Cl)Cl>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]1([C:19]2[NH:20][CH:21]=[CH:26][N:25]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 178517448HCID 178517448, compound

Product 1

HCID 70082524Phenyl imidazole biphenylYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 177 mg (0.148 mmol) of phenyl hydroxy imidazole (from Step 1) and 50 μL of pyridine in 1.5 mL of methylene chloride at 0° C. was added 32 μL of thionyl chloride, and the resulting brown solution was stirred at room temperature for 2 hour. The reaction mixture was washed with water, dried and concentrated in vacuo. The residue was purified over silica gel to give 105 mg (92%) of conjugated phenyl imidazole biphenyl as an oil which solidified upon standing.

Workup

  1. washThe reaction mixture was washed with water
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified over silica gel

Sources & evidence

ORD record
ord-d9deb038993b40a8a5a07aa087bc3760
Source dataset
uspto-grants-1995_06
Patent number
US05426105

Reaction notes

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