m-Chloroperbenzoic acid → HCID 13936019, compound

HRID 2292027Notes

Reaction equation

HRID 2292027 reaction equation
ClC1C=CC=C([C:8](OO)=[O:9])C=1.[CH3:12][C:13]1[NH:14][C:15](=[O:25])[CH2:16][S:17][C:18]=1[C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1>CO>[CH3:8][O:9][CH:16]1[C:15](=[O:25])[NH:14][C:13]([CH3:12])=[C:18]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)[S:17]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 30625322H-1,4-Thiazin-3(4H)-one, 5-methyl-6-(4-pyridinyl)-

Product 1

HCID 13936019HCID 13936019, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

m-Chloroperbenzoic acid (12 g) was added gradually to a stirred suspension of 5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one (10 g) in methanol (400 ml) under ice/water-cooling. The reaction mixture was further stirred at ambient temperature for 3 days. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate, was washed with saturated sodium bicarbonate aqueous solution and successively with water and was dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was dissolved in chloroform (about 50 ml) and was chromatographed on activated alumina (200 g, about 300 mesh, manufactured by Wako Pure Chemical Industries, Ltd.) cloumn, using chloroform as an eluant. The solvent was removed under reduced pressure and the residue was crystallized from ether to give the titled compound (6 g, yield 51.7%) as pale yellow powder.

Workup

  1. temperaturecooling
  2. customThe solvent was removed under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washwas washed with saturated sodium bicarbonate aqueous solution and successively with water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. dissolutionthe residue was dissolved in chloroform (about 50 ml)
  8. customwas chromatographed on activated alumina (200 g, about 300 mesh, manufactured by Wako Pure Chemical Industries, Ltd.) cloumn
  9. customThe solvent was removed under reduced pressure
  10. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-8d71fcf612a1416abb35f68afd40f0d0
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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