m-Chloroperbenzoic acid → 2-(6-Propylsulfinyl-2-pyridyl)-4H-1,3-benzothiazine-4-one

HRID 499306Notes

Reaction equation

HRID 499306 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:15][C:16]1[N:21]=[C:20]([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:18][CH:17]=1)[CH2:13][CH3:14]>C(OCC)(=O)C>[CH2:12]([S:15]([C:16]1[N:21]=[C:20]([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:18][CH:17]=1)=[O:9])[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22939404HCID 22939404, compound

Product 1

HCID 229395302-(6-Propylsulfinyl-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (ca. 50%, 0.17 g, 0.49 mmol) in ethyl acetate (20 ml) was added dropwise to a solution of 2-(6-propylthio-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.15 g, 0.48 mmol), which was obtained in Example 59, in ethyl acetate (50 ml) with stirring. The reaction mixture was stirred at room temperature for 18 hrs, washed with saturated aqueous sodium hydrogen carbonate solution (50 ml×2) and saturated brine, dried (MgSO4) and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give the titled compound (0.12 g, 76%) as crystals.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hrs
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution (50 ml×2) and saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c45fab8a832d450889d6aa0a514deba2
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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