Ethyl Acetate → HCID 59750173, compound

HRID 748358Notes

Reaction equation

HRID 748358 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:10]=[C:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[S:14][C:13]([C:21]2[N:26]=[C:25]([CH2:27]S([O-])(=O)=O)[CH:24]=[CH:23][CH:22]=2)=[N:12]1.C(OCC)(=O)C>CN(C=O)C.O>[N:5]1[CH:6]=[CH:7][C:2]([S:1][CH2:27][C:25]2[N:26]=[C:21]([C:13]3[S:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:11](=[O:10])[N:12]=3)[CH:22]=[CH:23][CH:24]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 865964626-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridylmethanesulfonateHCID 178418431pyridine-4-thiol

Product 1

HCID 59750173HCID 59750173, compoundYield 17.6%

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-pyridylmethanesulfonate (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-19a3359580f24e8f8332239024c9f114
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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