Dimethylformamide → 5-Bromo-3-(3-methoxyphenylthio)picolinonitrile

HRID 335232

反応式

HRID 335232 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([N+]([O-])=O)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([SH:21])[CH:18]=[CH:19][CH:20]=1.CN(C=O)C.[H-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([S:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 849893-MethoxybenzenethiolHCID 27696985-Bromo-3-nitropyridine-2-carbonitrile

生成物 1

HCID 669947555-Bromo-3-(3-methoxyphenylthio)picolinonitrile収率 82%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A 10 mL round-bottomed flask was charged with 5-bromo-3-nitropicolinonitrile (300 mg, 1.31 mmol), 3-methoxybenzenethiol (0.150 mL, 1.31 mmol), and DMF (12 mL). NaH (37.8 mg, 1.58 mmol) was added and reaction stirred at room temperature for 10 minutes. The reaction was poured into water and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated. The resulting residue was purified on silica gel (10% EtOAc in Hexanes) to afford the title compound (345 mg, 81%).

後処理

  1. customreaction
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting residue was purified on silica gel (10% EtOAc in Hexanes)

出典と根拠

ORDレコード
ord-42fbcbf997444d6dadb900bddb096fd9
出典データセット
uspto-grants-2014_11
特許番号
US08883828B2

関連ノート

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