m-Chloroperbenzoic acid → 2-methoxy-5-methyl-2H-1,4-thiazin-3(4H)-one

HRID 1381899Notes

Reaction equation

HRID 1381899 reaction equation
ClC1C=CC=C([C:8](OO)=[O:9])C=1.[CH3:12][C:13]1[NH:14][C:15](=[O:19])[CH2:16][S:17][CH:18]=1>CO>[CH3:8][O:9][CH:16]1[C:15](=[O:19])[NH:14][C:13]([CH3:12])=[CH:18][S:17]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 2900175-Methyl-2h-1,4-thiazin-3(4h)-one

Product 1

HCID 143697982-methoxy-5-methyl-2H-1,4-thiazin-3(4H)-oneYield 61.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

m-Chloroperbenzoic acid (28.8 g) was added dropwise to a stirred solution of 5-methyl-2H-1,4-thiazin-3(4H)-one (15 g) in methanol (300 ml) under ice-cooling and the mixture was stirred at room temperature for 1 day. After the mixture was evaporated to dryness, the residue was extracted with ethyl acetate, washed with saturated sodium bicarbonate aqueous solution and dried over anhydrous magnesium sulfate. The solvent was evaporated to dryness to give 2-methoxy-5-methyl-2H-1,4-thiazin-3(4H)-one (11.3 g, yield 61%) as pale yellow powder.

Workup

  1. temperaturecooling
  2. customAfter the mixture was evaporated to dryness
  3. extractionthe residue was extracted with ethyl acetate
  4. washwashed with saturated sodium bicarbonate aqueous solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-5a9e8f87d0e84e33951412dd4fb6b6b7
Source dataset
uspto-grants-1989_02
Patent number
US04804668

Reaction notes

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