Ethyl Acetate → HCID 59750431, compound

HRID 499526Notes

Reaction equation

HRID 499526 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].[H-].[Na+].CS(O[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[S:21][C:22]3[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=3[C:24](=[O:26])[N:25]=2)[N:15]=1)(=O)=O.[C:31](OCC)(=O)C>CN(C=O)C.O>[O:26]=[C:24]1[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[S:21][C:20]([C:16]2[N:15]=[C:14]([CH2:31][S:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])[CH:19]=[CH:18][CH:17]=2)=[N:25]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 16907Methyl ThioglycolateHCID 24758Sodium hydrideHCID 229392726-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate

Product 1

HCID 59750431HCID 59750431, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl thioglycolate (0.35 g, 3.30 mmol) and sodium hydride (60% in oil, 0.15 g, 3.60 mmol) were dissolved in DMF (30 ml), and 6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate (1.05 g, 3.00 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 (0.55 g, 51%) 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-c00d28209cae4731a90d6bbe7d37473f
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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