Ethyl Acetate → 2-Cyano-6-(3-phenylpropylthio)pyridine

HRID 748230Notes

Reaction equation

HRID 748230 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][SH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[N:15]=1.C(OCC)(=O)C>C1COCC1.O>[C:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([S:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:15]=1)#[N:21]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 905963-Phenylpropane-1-thiolHCID 1184246-Chloropyridine-2-carbonitrile

Product 1

HCID 229393782-Cyano-6-(3-phenylpropylthio)pyridineYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3-Phenylpropylmercaptan (1.21 g, 7.94 mmol) and sodium hydride (60%, 0.35 g, 8.66 mmol) were added to THF (30 ml), and the mixture was stirred at room temperature for 1 hr. A solution of 2-chloro-6-cyanopyridine (1.00 g, 7.22 mmol) in THF (10 ml) was added dropwise to the mixture and the mixture was stirred at room temperature for 18 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (1.84 g, 100%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hrs
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-10d34b57eaf64cbfb88e22a675ca35ea
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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