m-Chloroperbenzoic acid → HCID 86596458, compound

HRID 499301Notes

Reaction equation

HRID 499301 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[N:12]=2)=[CH:3][CH:2]=1.ClC1C=CC=C(C(OO)=[O:26])C=1>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]3[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[N+:12]=2[O-:26])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10130981HCID 10130981, compound

Product 1

HCID 86596458HCID 86596458, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(4-pyridyl)-4H-1,3-benzothiazine-4-one (1.00 g, 4.1 mmol) was dissolved in chloroform (20 ml). To the mixture was added 3-chloroperbenzoic acid (ca. 77%, 0.92 g, 4.1 mmol). The reaction mixture was stirred at room temperature for 24 hr and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography and eluted with ethyl acetate-methanol (20:1, v/v) and recrystallized from diisopropylether-methanol to give the titled compound (0.18 g, 16%) as crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washeluted with ethyl acetate-methanol (20:1
  3. customv/v) and recrystallized from diisopropylether-methanol

Sources & evidence

ORD record
ord-f221f308728c44b0889e5deb1013a665
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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