m-Chloroperbenzoic acid → HCID 59750307, compound

HRID 748114Notes

Reaction equation

HRID 748114 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[CH:6]=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[N:8]=[C:7]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[CH:6]=[CH:5][CH:4]=1)=[O:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 22939568HCID 22939568, compound

Product 1

HCID 59750307HCID 59750307, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-(6-Methylthio-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.28 g, 1.0 mmol) obtained in Example 43 was dissolved in chloroform (30 ml). To the stirred mixture was added dropwise a solution of 3-chloroperbenzoic acid (ca. 70%, 0.25 g, 1.0 mmol) in chloroform (10 ml). The reaction mixture was stirred for 1 hr and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with 10% methanol-chloroform and recrystallized from ethanol to give the titled compound (0.19 g, 64%) as crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washeluted with 10% methanol-chloroform
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-287bbe78db41457d9477b75445898cd5
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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