Potassium Carbonate → 2,2-dimethoxy-5-methyl-4H-1,4-thiazin-3-one

HRID 1381900Notes

Reaction equation

HRID 1381900 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])=[CH:16][S:15]1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:12][O:13][C:14]1([O:9][CH3:8])[C:19](=[O:20])[NH:18][C:17]([CH3:21])=[CH:16][S:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 143697982-methoxy-5-methyl-2H-1,4-thiazin-3(4H)-one

Product 1

HCID 143697992,2-dimethoxy-5-methyl-4H-1,4-thiazin-3-oneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

m-Chloroperbenzoic acid (25.6 g) was added dropwise to a stirred solution of 2-methoxy-5-methyl-2H-1,4-thiazin-3(4H)-one (16 g) in methanol (500 ml) under ice-cooling and the mixture was stirred at room temperature for 4 hours. Then, the reaction mixture was made alkaline by addition of anhydrous potassium carbonate and evaporated to dryness. The residue was extracted twice with chloroform and the combined extracts were washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was triturated with ethyl ether to give 2,2-dimethoxy-5-methyl-2H-1,4-thiazin-3(4H)-one (10 g, yield 53%) as pale yellow plates.

Workup

  1. temperaturecooling
  2. customevaporated to dryness
  3. extractionThe residue was extracted twice with chloroform
  4. washthe combined extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. customThe residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-b9a8df7e12b347659a93d414bcbb4014
Source dataset
uspto-grants-1989_02
Patent number
US04804668

Reaction notes

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