Thiophenol → 2-Chloro-5-(phenylthio)pyridine

HRID 45241

반응식

HRID 45241 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C[O-].[Na+]>CO.[OH-].[Na+].[Cu]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][N:3]=1

참가 물질

7

반응물 3

HCID 7969ThiophenolHCID 43971762-Chloro-5-iodopyridineHCID 10942334Sodium Methoxide

생성물 1

HCID 111953972-Chloro-5-(phenylthio)pyridine수율 60%

시약·촉매·용매 3

HCID 23978Copper촉매HCID 887Methanol용매HCID 14798Sodium Hydroxide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 3.4 g (14.3 mmol) of 2-chloro-5 iodopyridine, 1.9 g (17.2 mmol) of thiophenol, 0.93 g (17.2 mmol) of sodium methoxide and 0.36 g (5.7 mmol) of copper in 18 mL of MeOH is heated for 12 hours at 80° C. After cooling to room temperature, the medium is taken up in 100 mL of 1N NaOH and the MeOH is evaporated off under reduced pressure. The reaction medium is extracted with EtOAc (2×100 mL), the organic phase is washed with 0.1N NaOH (2×30 mL), and then dried over Na2SO4, concentrated under reduced pressure and purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc mixture (8/2). 1.90 g of 2-chloro-5-(phenylsulfanyl)pyridine are obtained in the form of a white powder.

후처리

  1. temperatureAfter cooling to room temperature
  2. customthe MeOH is evaporated off under reduced pressure
  3. extractionThe reaction medium is extracted with EtOAc (2×100 mL)
  4. washthe organic phase is washed with 0.1N NaOH (2×30 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. custompurified by chromatography on a column of silica gel
  8. washeluting with a cyclohexane/EtOAc mixture (8/2)

출처 및 근거

ORD 기록
ord-54549360e77f43089666cb6f25cc9bf9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541455B2

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