m-Chloroperbenzoic acid → HCID 59750161, compound

HRID 499307Notes

Reaction equation

HRID 499307 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([S:15]([C:17]1[N:22]=[C:21]([C:23]2[S:24][C:25]3[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=3[C:27](=[O:29])[N:28]=2)[CH:20]=[CH:19][CH:18]=1)=[O:16])[CH2:13][CH3:14]>C(OCC)(=O)C>[CH2:12]([S:15]([C:17]1[N:22]=[C:21]([C:23]2[S:24][C:25]3[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=3[C:27](=[O:29])[N:28]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:9])=[O:16])[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 229395302-(6-Propylsulfinyl-2-pyridyl)-4H-1,3-benzothiazine-4-one

Product 1

HCID 59750161HCID 59750161, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (ca. 50%, 0.44 g, 1.2 mmol) in ethyl acetate (10 ml) was added dropwise to a solution of 2-(6-propylsulfinyl-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.20 g, 0.64 mmol), which was obtained in Example 60, 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 ethanol to give the titled compound (0.09 g, 41%) 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 ethanol

Sources & evidence

ORD record
ord-6bbda1dc407d4de3920414178f5d748d
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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