Water → HCID 22939303, compound

HRID 499416Notes

Reaction equation

HRID 499416 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[N:17]=[C:16]([CH2:18][S:19]([O-])(=O)=O)[CH:15]=[CH:14][CH:13]=2)=[N:3]1.C[S-].[Na+].[C:26](OCC)(=O)C.O>CN(C=O)C>[CH3:26][S:19][CH2:18][C:16]1[N:17]=[C:12]([C:4]2[S:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2](=[O:1])[N:3]=2)[CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 865964626-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridylmethanesulfonate

Product 1

HCID 22939303HCID 22939303, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methane sulfonate (0.55 g, 1.58 mmol) was dissolved in DMF (30 ml), and sodium thiomethoxide (0.13 g, 1.74 mmol) was added thereto. The mixture was stirred at 70° C. for 3 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was recrystallized from ethanol to give the titled compound (0.35 g, 75%) 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-5cff22580cb84da4ba4e8924ddddc05d
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

Loading…