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

HRID 748343Notes

Reaction equation

HRID 748343 reaction equation
[CH2:1]([S:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)(Cl)Cl>[CH2:1]([S:8]([CH2:9][C:10]1[N:15]=[C:14]([C:16]2[S:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](=[O:22])[N:21]=2)[CH:13]=[CH:12][CH:11]=1)=[O:35])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59750208HCID 59750208, compound

Product 1

HCID 597503982-[6-[(Benzylsulfinyl)methyl]-2-pyridyl]-4H-1,3-benzothiazine-4-oneYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-[6-[(Benzylthio)methyl]-2-pyridyl]-4H-1,3-benzothiazine-4-one (0.080 g, 0.22 mmol) was dissolved in chloroform (50 ml), and a solution of 3-chloroperbenzoic acid (ca. 77%, 0.037 g, 0.22 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 n-hexane-ethyl acetate to give the titled compound (0.053 g, 64%) as pale yellow crystals.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was recrystallized from n-hexane-ethyl acetate

Sources & evidence

ORD record
ord-5725993e06ae4bb4a66b102f1985ab85
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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