Imidazole → 1-[([1,1'-Biphenyl]-4-yl)(2-chlorophenyl)methyl]-1H-imidazole

HRID 1111660Notes

Reaction equation

HRID 1111660 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C[O-].[Na+].[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)Cl>C(#N)C>[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10942334Sodium MethoxideHCID 22767075HCID 22767075, compound

Product 1

HCID 717421-[([1,1'-Biphenyl]-4-yl)(2-chlorophenyl)methyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 13.6 g (0.2 mol) of imidazole in 100 ml of acetonitrile is added dropwise to a suspension of 10.8 g (0.13 mol) of sodium methylate in 200 ml of acetonitrile. The resulting sodium imidazole is filtered off and suspended in 300 ml of acetonitrile, and 31.3 g (0.1 mol) of (2-chlorophenyl)-(biphenyl-4-yl)-chloromethane are added. After heating for 24 hours to 80° C., the mixture is allowed to cool, and is filtered. The filtrate is freed from the solvent by distilling the latter off in vacuo. The oil which remains is dissolved in ethyl acetate and the solution is washed with water, dried over sodium sulfate, filtered and freed from the solvent in vacuo. The oily residue is dissolved in chloroform and chromatographed on a silica gel column. After separating off a chloroform fraction containing a compound of melting point 150° C., the chloroform fraction containing desired end product is obtained. After distilling off the solvent, 10.7 g (31% of theory) of (2-chlorophenyl)imidazol-1-yl-(biphenyl-4-yl)-methane of melting point 90° C. are obtained.

Workup

  1. filtrationThe resulting sodium imidazole is filtered off
  2. temperatureAfter heating for 24 hours to 80° C.
  3. temperatureto cool
  4. filtrationis filtered
  5. distillationby distilling the latter off in vacuo
  6. dissolutionThe oil which remains is dissolved in ethyl acetate
  7. washthe solution is washed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. dissolutionThe oily residue is dissolved in chloroform
  11. customchromatographed on a silica gel column
  12. customAfter separating off a chloroform fraction
  13. additioncontaining a compound of melting point 150° C.
  14. additionthe chloroform fraction containing desired end product
  15. customis obtained
  16. distillationAfter distilling off the solvent, 10.7 g (31% of theory) of (2-chlorophenyl)imidazol-1-yl-(biphenyl-4-yl)-methane of melting point 90° C.
  17. customare obtained

Sources & evidence

ORD record
ord-818c891b42b24e7eba02e46f726b9aed
Source dataset
uspto-grants-1978_10
Patent number
US04118487

Reaction notes

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