Imidazole → Bifonazole

HRID 1111657

反応式

HRID 1111657 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 2378Bifonazole

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9b15d528063b40abb29e802c515022ea
出典データセット
uspto-grants-1978_10
特許番号
US04118487

関連ノート

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