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

HRID 335232

반응식

HRID 335232 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 669947555-Bromo-3-(3-methoxyphenylthio)picolinonitrile수율 82%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-42fbcbf997444d6dadb900bddb096fd9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883828B2

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