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

HRID 499415Notes

Reaction equation

HRID 499415 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][S:10][C:11]2[N:16]=[C:15]([C:17]3[S:18][C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21](=[O:23])[N:22]=3)[CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:36])C=1>C(Cl)(Cl)Cl>[C:1]1([CH2:7][CH2:8][CH2:9][S:10]([C:11]2[N:16]=[C:15]([C:17]3[S:18][C:19]4[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=4[C:21](=[O:23])[N:22]=3)[CH:14]=[CH:13][CH:12]=2)=[O:36])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 597504222-[6-(3-Phenylpropyl)thio-2-pyridyl]-4H-1,3-benzothiazine-4-one

Product 1

HCID 597504702-[6-[(3-Phenylpropyl)sulfinyl]-2-pyridyl]-4H-1,3-benzothiazine-4-oneYield 31%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-[6-(3-Phenylpropyl)thio-2-pyridyl]-4H-1,3-benzothiazine-4-one (0.20 g, 0.50 mmol) was dissolved in chloroform (30 ml), and a solution of 3-chloroperbenzoic acid (ca. 70%, 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 (0.063 g, 31%) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-084ae583d5134909a9773e28a2fc68dd
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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