m-Chloroperbenzoic acid → HCID 59750185, compound

HRID 748129Notes

Reaction equation

HRID 748129 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([C:21]2[N:26]=[C:25]([C:27]3[S:28][C:29]4[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=4[C:31](=[O:33])[N:32]=3)[CH:24]=[CH:23][CH:22]=2)=[O:20])=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH3:12][C:13]1[CH:14]=[CH:15][C:16]([S:19]([C:21]2[N:26]=[C:25]([C:27]3[S:28][C:29]4[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=4[C:31](=[O:33])[N:32]=3)[CH:24]=[CH:23][CH:22]=2)(=[O:9])=[O:20])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59750483HCID 59750483, compound

Product 1

HCID 59750185HCID 59750185, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 3-chloroperbenzoic acid (ca. 70%, 0.53 g, 2.1 mmol) in chloroform (10 ml) was added dropwise to a solution of 2-{6-[(4-methylphenyl)sulfinyl]-2-pyridyl}-4H-1,3-benzothiazine-4-one (0.35 g, 11.0 mmol) in chloroform (50 ml) with stirring. The reaction mixture was stirred at room temperature for 5 hrs and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography, eluted with hexane-ethyl acetate (1:1, v/v) and recrystallized from ethanol to give the titled compound (0.25 g, 64%) as crystals.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 hrs
  2. concentrationconcentrated under reduced pressure
  3. washeluted with hexane-ethyl acetate (1:1
  4. customv/v) and recrystallized from ethanol

Sources & evidence

ORD record
ord-47299156e9df4d8cac5cfe9ea15a2ba5
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Reaction notes

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