Hydrochloric Acid → 6-mercapto-2H-1,4-benzoxazin-3(4H)-one

HRID 1192257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192257
[O:1]=[C:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][C:10]([S:12](Cl)(=O)=O)=[CH:11][C:4]=2[NH:3]1.Cl.[Sn].C(OCC)(=O)C>O1CCOCC1>[SH:12][C:10]1[CH:9]=[CH:8][C:5]2[O:6][CH2:7][C:2](=[O:1])[NH:3][C:4]=2[CH:11]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 52002293-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-sulfonyl chlorideHCID 5352426Tin atom

Produkt 1

HCID 162277896-mercapto-2H-1,4-benzoxazin-3(4H)-oneAusbeute 16,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-sulfonyl chloride (5.8 g, 20.2 mmol), was added the hydrogen chloride in 1,4-dioxane (30 mL) followed by tin powder (12 g, 10.1 mmol). The resulting mixture was heated under reflux for 2 hours. After this time, the solvent of the reaction mixture was removed under vacuum to give the crude residue. The resulting residue was treated with ethyl acetate and washed with brine and water. The organic layer was separated, dried (Na2SO4) and concentrated. The crude material was purified by silica gel chromatography using a 60:40 mixture of hexane and ethyl acetate as eluent to afford the title product as a white solid (0.59 g, 16% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.82 (1H, s), 6.86 (2H, m), 6.81 (1H, m), 5.40 (1H, s), 4.53 (2H, s).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customAfter this time, the solvent of the reaction mixture was removed under vacuum
  4. customto give the crude residue
  5. washwashed with brine and water
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by silica gel chromatography
  10. additiona 60:40 mixture of hexane and ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-f92917e49b9b4f7392d5cfea292906fd
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680139B2

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