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

HRID 911644ノート

反応式

HRID 911644 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 284131906-(Tert-butylsulfanyl)pyridine-3-carbonitrile収率 91.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-1cd07deb21fe409bb4588cc3c30b815c
出典データセット
uspto-grants-2011_09
特許番号
US08022062B2

反応ノート

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