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

HRID 499411Notes

Reaction equation

HRID 499411 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]([C:15]2[S:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[N:20]=2)[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>C(Cl)(Cl)Cl>[CH2:1]([S:8]([C:9]1[N:14]=[C:13]([C:15]2[S:16][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[N:20]=2)[CH:12]=[CH:11][CH:10]=1)=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 229395932-(6-Benzylthio-2-pyridyl)-4H-1,3-benzothiazine-4-one

Product 1

HCID 597502972-(6-Benzylsulfinyl-2-pyridyl)-4H-1,3-benzothiazine-4-oneYield 30.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-(6-Benzylthio-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.18 g, 0.50 mmol) was dissolved in chloroform (30 ml), and a solution of 3-chloroperbenzoic acid (ca. 77%, 0.11 g, 0.50 mmol) in chloroform (10 ml) was added dropwise thereto. The reaction 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 (0.057 g, 30%) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-3c19b6263ad3467eb1969aa72b49ea70
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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