Water → HCID 22939303, compound

HRID 748233Notes

Reaction equation

HRID 748233 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]methanesulfonate (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-08c2559a54b24541ae444743e5af66ac
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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