Ethyl Acetate → HCID 59750173, compound

HRID 499540Notes

Reaction equation

HRID 499540 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[H-].[Na+].CS(O[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]2[S:22][C:23]3[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=3[C:25](=[O:27])[N:26]=2)[N:16]=1)(=O)=O.[C:32](OCC)(=O)C>CN(C=O)C.O>[N:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:32][C:15]2[N:16]=[C:17]([C:21]3[S:22][C:23]4[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=4[C:25](=[O:27])[N:26]=3)[CH:18]=[CH:19][CH:20]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 229392726-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonateHCID 178418431pyridine-4-thiol

Product 1

HCID 59750173HCID 59750173, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Mercaptopyridine (0.21 g, 1.89 mmol) and sodium hydride (60% in oil, 0.083 g, 2.06 mmol) were dissolved in DMF (30 ml), and 6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate (0.60 g, 1.72 mmol) was added thereto. The reaction mixture was stirred at room temperature 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 ethanol to give the titled compound (0.11 g, 17%) as pale yellow crystals.

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 ethanol

Sources & evidence

ORD record
ord-8ab020583f7f47b1beaa5713dd245601
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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