Benzyl mercaptan → HCID 59750208, compound

HRID 499524Notes

Reaction equation

HRID 499524 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].CS(O[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[S:23][C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[C:26](=[O:28])[N:27]=2)[N:17]=1)(=O)=O.[C:33](OCC)(=O)C>CN(C=O)C.O>[CH2:1]([S:8][CH2:33][C:16]1[N:17]=[C:18]([C:22]2[S:23][C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[C:26](=[O:28])[N:27]=2)[CH:19]=[CH:20][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 229392726-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl methanesulfonate

Product 1

HCID 59750208HCID 59750208, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benzyl mercaptan (0.41 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 n-hexane-ethyl acetate to give the titled compound (0.18 g, 16%) 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 n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-79f398647a1b4d08bf1c2dd9b270e40c
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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