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

HRID 588789

반응식

HRID 588789 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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]−.

후처리

  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)

출처 및 근거

ORD 기록
ord-72729ac48648442da4a5385bfc265a6b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227978B2

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