Benzyl mercaptan → HCID 59750208, compound

HRID 748342Notes

Reaction equation

HRID 748342 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[O:11]=[C:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[S:15][C:14]([C:22]2[N:27]=[C:26]([CH2:28]S([O-])(=O)=O)[CH:25]=[CH:24][CH:23]=2)=[N:13]1.C(OCC)(=O)C>CN(C=O)C.O>[CH2:1]([S:8][CH2:28][C:26]1[N:27]=[C:22]([C:14]2[S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:12](=[O:11])[N:13]=2)[CH:23]=[CH:24][CH:25]=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 865964626-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridylmethanesulfonate

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-pyridylmethanesulfonate (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-fdf9ed21b5ab46d38d36f80ebc36299d
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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