m-Chloroperbenzoic acid → 2,2-Dimethoxy-5-methyl-6-(pyridin-4-yl)-2H-1,4-thiazin-3(4H)-one

HRID 2292028Notes

Reaction equation

HRID 2292028 reaction equation
ClC1C=CC=C([C:8](OO)=[O:9])C=1.[CH3:12][O:13][CH:14]1[C:19](=[O:20])[NH:18][C:17]([CH3:21])=[C:16]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[S:15]1>CO>[CH3:12][O:13][C:14]1([O:9][CH3:8])[C:19](=[O:20])[NH:18][C:17]([CH3:21])=[C:16]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=2)[S:15]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13936019HCID 13936019, compound

Product 1

HCID 139360292,2-Dimethoxy-5-methyl-6-(pyridin-4-yl)-2H-1,4-thiazin-3(4H)-oneYield 66.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

m-Chloroperbenzoic acid (2.8 g) was added to a stirred solution of 2 -methoxy-5-methyl-6-(4-pyridinyl)-2H-1,4-thiazin-3(4H)-one (2.7 g) in methanol (100 ml) under ice/water-cooling. The reaction mixture was further stirred at ambient temperature for 2 hours. Methanol was removed under reduced pressure and the residue was dissolved in ethyl acetate, was washed with saturated sodium bicarbonate aqueous solution and successively with water, and was dried over magnesium sulfate. Ethyl acetate was removed under reduced pressure and the residue was crystallized from ether to give the titled compound (2 g, yield 66.7%) as pale yellow powder.

Workup

  1. temperaturecooling
  2. customMethanol was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwas washed with saturated sodium bicarbonate aqueous solution and successively with water
  5. dry with materialwas dried over magnesium sulfate
  6. customEthyl acetate was removed under reduced pressure
  7. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-e184bec38aa14531903c79e96f7b8d90
Source dataset
uspto-grants-1989_01
Patent number
US04800201

Reaction notes

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