m-Chloroperbenzoic acid → Methyl ({[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl}sulfinyl)acetate

HRID 748345Notes

Reaction equation

HRID 748345 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][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:15]=[CH:14][CH:13]=2)=[N:3]1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[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]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[O:33])[CH:15]=[CH:14][CH:13]=2)=[N:3]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59750431HCID 59750431, compound

Product 1

HCID 59750277Methyl ({[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl}sulfinyl)acetateYield 92%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

Methyl ({[6-(4-oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]methyl}thio)acetate (0.10 g, 0.28 mmol) was dissolved in chloroform (50 ml), and a solution of 3-chloroperbenzoic acid (ca. 77%, 0.064 g, 0.28 mmol) in chloroform (10 ml) was added dropwise thereto. The mixture was stirred at room temperature for 1 hr. The solvent was evaporated, and the residue was recrystallized from ethanol to give the titled compound (0.096 g, 92%) as pale yellow crystals.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f0ea58a5c14347658825b252a8ca36d4
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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