Dimethylformamide → HCID 22939381, compound

HRID 499535Notes

Reaction equation

HRID 499535 reaction equation
[SH:1][C:2]1C=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Cl[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[N:18])[N:12]=1.C(OCC)(=O)C.C[N:26](C=O)C>O>[C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([S:1][C:2]2[N:26]=[CH:6][CH:5]=[CH:4][N:3]=2)[N:12]=1)#[N:18]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 1184246-Chloropyridine-2-carbonitrileHCID 178418616HCID 178418616, compound

Product 1

HCID 22939381HCID 22939381, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

2-Mercaptopyridine (0.89 g, 7.94 mmol) and sodium hydride (60% in oil, 0.35 g, 8.66 mmol) were dissolved in DMF (30 ml), and 2-chloro-6-cyanopyridine (1.05 g, 3.00 mmol) was added thereto. The reaction mixture was stirred at 70° C. for 18 hrs and combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from n-hexane-ethyl acetate to give the titled compound (1.32 g, 85%).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-6307e22304c94afbb140947426f6755a
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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