Sodium hydride → 2-(4-Chloropyridin-2-yloxy)-4,5-dichlorobenzenamine

HRID 588789ノート

反応式

HRID 588789 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[OH:10].[H-].[Na+].[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16](F)[CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:10][C:3]2[CH:4]=[C:5]([Cl:9])[C:6]([Cl:8])=[CH:7][C:2]=2[NH2:1])[CH:15]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27628394-Chloro-2-fluoropyridineHCID 30154152-Amino-4,5-dichlorophenol

生成物 1

HCID 1176071602-(4-Chloropyridin-2-yloxy)-4,5-dichlorobenzenamine収率 45%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-amino-4,5-dichlorophenol (1.5 g, 8.47 mmol) in THF (20 mL) at 0° C., NaH (60% dispersed in oil, 373 mg, 9.33 mmol) was added and the resulting mixture was stirred for 20 min. To this mixture, 4-chloro-2-fluoropyridine (1.67 g, 12.7 mmol) was added and the resulting mixture was stirred at reflux under argon for 15 h. The mixture was allowed to cool to room temperature and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 10:1) to afford the desired product (1.1 g, 45% yield). ESI-MS m/z: 287.0 [M−H]−.

後処理

  1. stirringthe resulting mixture was stirred
  2. temperatureat reflux under argon for 15 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel (petroleum ether/ethyl acetate=20:1 to 10:1)

出典と根拠

ORDレコード
ord-72729ac48648442da4a5385bfc265a6b
出典データセット
uspto-grants-2016_01
特許番号
US09227978B2

反応ノート

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