Imidazole → Bifonazole

HRID 1111657

Reaction equation

HRID 1111657 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O.[C:10]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=[CH:14][C:13]([CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)O)=[CH:12][CH:11]=1.S(C1NC=CN=1)(C1NC=CN=1)=O>C(#N)C>[C:10]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:11]=[CH:12][C:13]([CH:16]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 95512alpha-Phenyl[1,1'-biphenyl]-4-methanolHCID 21946057Thionyldiimidazole

Product 1

HCID 2378Bifonazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13.6 g (0.2 mol) of imidazole are dissolved in 150 ml of acetonitrile and 3.5 ml of thionyl chloride are added at 10° C. 13 g (0.05 mol) of (biphenyl-4-yl)-phenyl-carbinol are added to the solution of thionyl-bis-imidazole thus obtained. After standing for 15 hours at room temperature, the solvent is removed by distillation in vacuo. The residue is taken up in chloroform and the solution is washed with water. The organic phase is collected, dried over sodium sulfate and filtered and the solvent is distiller off in vacuo. The oily residue is dissolved in ethyl acetate and freed from insoluble, resinous constituents by filtration. The solvent is again distilled off in vacuo and the residue is purified by recrystallization from acetonitrile. 8.7 g (56% of theory) of (biphenyl-4-yl)-imidazol-1-yl-phenylmethane [alternatively named as diphenyl-imidazolyl-(1)-phenyl-methane or as 1-(α-biphenyl-4-ylbenzyl)imidazole] of melting point 142° C. are obtained.

Workup

  1. customthus obtained
  2. customthe solvent is removed by distillation in vacuo
  3. washthe solution is washed with water
  4. customThe organic phase is collected
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. dissolutionThe oily residue is dissolved in ethyl acetate
  8. filtrationby filtration
  9. distillationThe solvent is again distilled off in vacuo
  10. customthe residue is purified by recrystallization from acetonitrile
  11. customare obtained

Sources & evidence

ORD record
ord-9b15d528063b40abb29e802c515022ea
Source dataset
uspto-grants-1978_10
Patent number
US04118487

Linked notes

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