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Dimethylformamide → 5-bromo-2-(phenylthio)pyridine

HRID 1691188
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HRID 1691188 반응식
CN(C)C=O.[C:6]1([SH:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[Na+].Br[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=1>O>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([S:12][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:17][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 693532,5-Dibromopyridine

생성물 1

HCID 221806675-bromo-2-(phenylthio)pyridine수율 99.7%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To an N,N-dimethylformamide (20 mL) solution of thiophenol (1.02 g, 9.28 mmol) was added sodium hydride (446 mg, 9.28 mmol, 50% in oil), which was stirred for 15 minutes at room temperature. 2,5-Dibromopyridine (2.00 g, 8.44 mmol) was then added to this reaction mixture and stirred for 35 minutes at room temperature, and then for a further 45 minutes at 55° C. Water was added to the reaction solution at room temperature, which was then extracted with ethyl acetate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (heptane:ethyl acetate:=4:1) to obtain the title compound (2.24 g, quant.).

후처리

  1. stirringstirred for 35 minutes at room temperature
  2. waitfor a further 45 minutes at 55° C
  3. extractionwhich was then extracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under a reduced pressure
  9. customthe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate:=4:1)

출처 및 근거

ORD 기록
ord-cb0f0d75f0334e0696d10ef2f877e13a
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08153662B2

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