m-Chloroperbenzoic acid → 2-[2-(Methylsulfinyl)-6-pyrimidinyl]-4H-1,3-benzothiazine-4-one

HRID 499553Notes

Reaction equation

HRID 499553 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[CH:7][CH:6]=[C:5]([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)[N:4]=1.ClC1C=CC=C(C(OO)=[O:28])C=1>C(Cl)(Cl)Cl>[CH3:1][S:2]([C:3]1[N:8]=[CH:7][CH:6]=[C:5]([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)[N:4]=1)=[O:28]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 597502412-[2-(Methylthio)-6-pyrimidinyl]-4H-1,3-benzothiazine-4-one

Product 1

HCID 597500942-[2-(Methylsulfinyl)-6-pyrimidinyl]-4H-1,3-benzothiazine-4-oneYield 55%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-[2-(Methylthio)-6-pyrimidinyl]-4H-1,3-benzothiazine-4-one (0.30 g, 1.50 mmol) was dissolved in chloroform (100 ml), and a solution of 3-chloroperbenzoic acid (ca. 77%, 0.23 g, 1.50 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 (0.18 g, 55%) as pale yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-dd1f1fc04d494350836797ecc5731d31
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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