Sodium hydride → HCID 67485570、化合物

HRID 534079ノート

反応式

HRID 534079 の反応式
[CH2:1]([C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2].[H-].[Na+].Br[C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.[NH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]1=[S:30]>CN(C=O)C>[CH2:1]([C:3]1[C:8]([O:9][C:15]2[C:16]([C:19]#[N:20])=[N:17][CH:18]=[C:13]([S:30][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][N:24]=3)[CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:2]

参加物

6

反応物 4

HCID 24758Sodium hydride2 回HCID 27236982-MercaptopyridineHCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 38372322-Ethylpyridin-3-ol

生成物 1

HCID 67485570HCID 67485570、化合物収率 108.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Ethylpyridin-3-ol (27.5 g, 223 mmol) was dissolved in DMF (900 mL) and cooled in an ice bath. 60% Sodium hydride (8.93 g, 223 mmol) was added portionwise and stirred in an ice bath for 30 minutes. 5-Bromo-3-nitropicolinonitrile (50.9 g, 223 mmol) was added in one portion and the fraction was stirred in an ice bath for 1 hour. Pyridine-2(1H)-thione (24.8 g, 223 mmol) was added, followed by 60% sodium hydride (8.93 g, 223 mmol) and reaction was stirred in an ice bath slowly warming to ambient temperature overnight. The reaction was concentrated in vacuo to about 300 mL and poured into 3 L water with vigorous stirring. The mixture was extracted with EtOAc, washed with water and brine, dried over sodium sulfate, filtered and concentrated to afford 3-(2-ethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (81 g, 242 mmol, 108% yield) as a dark oil.

後処理

  1. temperaturecooled in an ice bath
  2. stirringthe fraction was stirred in an ice bath for 1 hour
  3. stirringwas stirred in an ice bath
  4. concentrationThe reaction was concentrated in vacuo to about 300 mL
  5. additionpoured into 3 L water with vigorous stirring
  6. extractionThe mixture was extracted with EtOAc
  7. washwashed with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-f5ad8062483c4c6c8d9c0fca72aa9999
出典データセット
uspto-grants-2014_10
特許番号
US08853409B2

反応ノート

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