Ethanethiol → HCID 59750265, compound

HRID 499521Notes

Reaction equation

HRID 499521 reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].CS(O[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[S:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21](=[O:23])[N:22]=2)[N:12]=1)(=O)=O.[C:28](OCC)(=O)C>CN(C=O)C.O>[CH2:1]([S:3][CH2:28][C:11]1[N:12]=[C:13]([C:17]2[S:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21](=[O:23])[N:22]=2)[CH:14]=[CH:15][CH:16]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 229392726-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate

Product 1

HCID 59750265HCID 59750265, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl mercaptan (0.25 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 magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from n-hexane-ethyl acetate to give the titled compound (0.23 g, 24%) as pale yellow crystals.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-b287563ef7a546bbb3f31890b83fc1e9
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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