Dimethylformamide → 2-Acetylthiomethylthiopyridine

HRID 249579Notes

Reaction equation

HRID 249579 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[S:10]1[CH:14]=C[CH:12]=[C:11]1CC(OCCl)=O.CN(C)C=[O:24]>C(OCC)(=O)C>[C:11]([S:10][CH2:14][S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)(=[O:24])[CH3:12]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 57186933Chloromethyl thiolacetateHCID 178418616HCID 178418616, compound

Product 1

HCID 104653712-AcetylthiomethylthiopyridineYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-mercaptopyridine (1.11 g : 9.98 mMol.) in dimethylformamide (10 ml) is added sodium hydride (400 mg : 60% dispersion in oil), and the mixture is stirred at room temperature for 2 to 3 minutes. To this reaction mixture at -30° C. is added a solution of chloromethyl thiolacetate (1.12 g : 9.00 mMol.) in dimethylformamide (2 ml), and the mixture is stirred at -20 to -30° C. for 1 hour. The reaction mixture is diluted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (toluene : ethyl acetate=20: 1) to give 2-acetylthiomethylthiopyridine (1.43 g) as yellow oil. Yield: 72%.

Workup

  1. stirringthe mixture is stirred at -20 to -30° C. for 1 hour
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel chromatography (toluene : ethyl acetate=20: 1)

Sources & evidence

ORD record
ord-3e93b749dbee45a298d71ca4f6995264
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Reaction notes

Loading…