Methyl iodide → 2,3,6-trimethyl-2H-1,2-thiazin-5(6H)-one 1,1-dioxide

HRID 1252254Notes

Reaction equation

HRID 1252254 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:9]([CH3:10])=[CH:8][C:7](=[O:11])[CH2:6][S:5]1(=[O:13])=[O:12].[CH3:14]I>O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[CH3:3][N:4]1[C:9]([CH3:10])=[CH:8][C:7](=[O:11])[CH:6]([CH3:14])[S:5]1(=[O:12])=[O:13]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 124708272,3-dimethyl-1,2-thiazin-5(6H)-one 1,1-dioxide

Product 1

HCID 201410512,3,6-trimethyl-2H-1,2-thiazin-5(6H)-one 1,1-dioxideYield 47.6%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.6 g of sodium hydroxide in 20 ml of water was added dropwise at 5°-12° with vigorous stirring to a solution of 3.5 g of 2,3-dimethyl-1,2-thiazin-5(6H)-one 1,1-dioxide, 6.8 g of tetrabutylammonium hydrogen sulfate and 1.9 ml (0.03 mol) of methyl iodide in 40 ml of methylene chloride. The mixture was thereafter stirred vigorously at room temperature for 15 minutes. The organic phase was separated, the aqueous phase was extracted twice with 15 ml of methylene chloride and the combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate and concentrated to dryness. The oily residue was chromatographed on 300 g of silica gel with chloroform/n-heptane/ethanol (10:10:1) as the elution agent. The uniform fractions were combined and evaporated. After triturating the residue with ether there were obtained 1.8 g of 2,3,6-trimethyl-2H-1,2-thiazin-5(6H)-one 1,1-dioxide in the form of colorless crystals, m.p. 73°-75°.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was extracted twice with 15 ml of methylene chloride
  3. washthe combined organic phases were washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe oily residue was chromatographed on 300 g of silica gel with chloroform/n-heptane/ethanol (10:10:1) as the elution agent
  7. customevaporated
  8. customAfter triturating the residue with ether

Sources & evidence

ORD record
ord-86ce807f7e114dfda2c7ac6d01f79d31
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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