Phenol → 2-Phenoxy-6-(phenylamino)benzonitrile

HRID 1826833

反応式

HRID 1826833 の反応式
[O-:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].C1(O)C=CC=CC=1.[H-].[Na+].F[C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:20]=1[C:21]#[N:22]>O1CCCC1.CS(C)=O>[O:1]([C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:20]=1[C:21]#[N:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 996PhenolHCID 24758Sodium hydrideHCID 4445035Phenolate SodiumHCID 134697992-Fluoro-6-(phenylamino)benzonitrile

生成物 1

HCID 221362262-Phenoxy-6-(phenylamino)benzonitrile

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
110 °C

実験手順

Sodium phenoxide was generated by dissolving phenol (0.36 g, 3.83 mmol) in dry tetrahydrofuran (5 mL), and adding sodium hydride (0.087 g, 3.6 mmol). After gas evolution ceased, the solvent was evaporated and 2-fluoro-6-(phenylamino)benzonitrile (0.6 g, 2.83 mmol) dissolved in dimethyl sulfoxide (10 mL) was added. The mixture was heated to 110° C. while stirring under argon for 4 hours. The solvent was evaporated in vacuo, and the residue was partitioned between ethyl acetate and water. The organic phase was washed with water (5×), brine (1×) dried over anhydrous Na2SO4 filtered, and evaporated to give the crude product which was then chromatographed on silica gel eluted with 10–40% CH2Cl2 in hexane to give the title compound as a white amorphous solid. mp 146–147° C.

後処理

  1. customthe solvent was evaporated
  2. additionwas added
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic phase was washed with water (5×), brine (1×)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product which
  10. customwas then chromatographed on silica gel
  11. washeluted with 10–40% CH2Cl2 in hexane

出典と根拠

ORDレコード
ord-a88a8d277a694ee585d5cae87833e4f4
出典データセット
uspto-grants-2006_05
特許番号
US07053099B1

関連ノート

読み込み中…