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

HRID 1252254Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1252254
[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]

Komponenten

7

Edukt 3

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

Produkt 1

HCID 201410512,3,6-trimethyl-2H-1,2-thiazin-5(6H)-one 1,1-dioxideAusbeute 47,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-86ce807f7e114dfda2c7ac6d01f79d31
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04742069

Notizen zur Reaktion

Wird geladen…