tert-Butyl mercaptan → 6-(Tert-butylsulfanyl)pyridine-3-carbonitrile

HRID 911644노트

반응식

HRID 911644 반응식
[O-]CC.[Na+].[CH3:5][C:6]([SH:9])([CH3:8])[CH3:7].Cl[C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=1.C([O-])(O)=O.[Na+]>C(O)C>[C:6]([S:9][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][N:12]=1)([CH3:8])([CH3:7])[CH3:5]

참가 물질

6

반응물 4

HCID 6387tert-Butyl mercaptanHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 51520946-Chloro-3-pyridinecarbonitrile

생성물 1

HCID 284131906-(Tert-butylsulfanyl)pyridine-3-carbonitrile수율 91.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Add sodium ethoxide (12 mL of 21% w/v in ethanol, 36 mmol) to a solution of 2-methyl-2-propanethiol (4.06 mL, 36 mmol) in anhydrous ethanol (90 mL) at 0° C. under nitrogen atmosphere. Stir the solution and allow it to warm to room temperature over 30 min. Add 6-chloronicotinonitrile (5 g, 36 mmol) and then heat the reaction to reflux overnight. Cool to room temperature, add saturated aqueous NaHCO3 and concentrate in vacuo. Extract into EtOAc or dichloromethane and wash with brine. Dry over MgSO4 and concentrate in vacuo to give the desired intermediate as orange crystals (6.31 g, 91%). MS (ES+) m/z: 193 (M+H)+.

후처리

  1. customthe reaction
  2. temperatureto reflux overnight
  3. temperatureCool to room temperature
  4. concentrationconcentrate in vacuo
  5. extractionExtract into EtOAc or dichloromethane
  6. washwash with brine
  7. dry with materialDry over MgSO4
  8. concentrationconcentrate in vacuo

출처 및 근거

ORD 기록
ord-1cd07deb21fe409bb4588cc3c30b815c
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022062B2

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