Ethyl Acetate → HCID 22939378, compound

HRID 499413Notes

Reaction equation

HRID 499413 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 22939378HCID 22939378, compoundYield 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-04771941510a4537b9719ffd2055fbaa
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…