tert-Butyl mercaptan → 864266-67-1

HRID 2041508Notes

Reaction equation

HRID 2041508 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 28413190864266-67-1Yield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-5506a3c3b2a24f24980350737590ca9e
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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