Ethyl Acetate → 2-Cyano-6-(1-methyl-1H-imidazol-2-yl)thiopyridine
Reaction equation
[SH:1][C:2]1[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=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>CN(C=O)C.O>[C:17]([C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([S:1][C:2]2[N:3]([CH3:7])[CH:4]=[CH:5][N:6]=2)[N:12]=1)#[N:18]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
2-Mercapto-1-methyl-1H-imidazole (0.91 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 (1.71 g, ca. 100%) as pale yellow crystals.
Workup
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated
- customthe residue was recrystallized from n-hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-99b20cab5ce8403285552e0902eba362
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07399759B2
Reaction notes
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