Ethanethiol → HCID 59750265, compound

HRID 748339Notes

Reaction equation

HRID 748339 reaction equation
[CH2:1]([SH:3])[CH3:2].[H-].[Na+].[O:6]=[C:7]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10][C:9]([C:17]2[N:22]=[C:21]([CH2:23]S([O-])(=O)=O)[CH:20]=[CH:19][CH:18]=2)=[N:8]1.C(OCC)(=O)C>CN(C=O)C.O>[CH2:1]([S:3][CH2:23][C:21]1[N:22]=[C:17]([C:9]2[S:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:7](=[O:6])[N:8]=2)[CH:18]=[CH:19][CH:20]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 865964626-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridylmethanesulfonate

Product 1

HCID 59750265HCID 59750265, compoundYield 24.4%

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-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 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-36f4a877093c4718aa77b0382a6de7f0
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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