6-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazine → 2-(6-bromo-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)-1,3-dithian-1-oxide

HRID 326597

Reaktionsgleichung

Reaktionsgleichung von HRID 326597
I([O-])(=O)(=O)=[O:2].[Na+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:15]([CH3:18])([CH3:17])[N:14]=[C:13]([CH:19]3[S:24][CH2:23][CH2:22][CH2:21][S:20]3)[C:12]=2[CH:25]=1>O.CO>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:16][C:15]([CH3:17])([CH3:18])[N:14]=[C:13]([CH:19]3[S:20][CH2:21][CH2:22][CH2:23][S:24]3=[O:2])[C:12]=2[CH:25]=1

Komponenten

5

Edukt 2

HCID 197350976-bromo-2,2-dimethyl-4-(1,3-dithian-2-yl)-2H-1,3-benzoxazineHCID 23667635Sodium periodate

Produkt 1

HCID 197351332-(6-bromo-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)-1,3-dithian-1-oxideAusbeute 52,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of sodium periodate (430 mg) in water (6 ml) was added to a solution of Compound 105 (600 mg) in methanol (18 ml) and the mixture was stirred at room temperature for 18 hours. The methanol was distilled off under reduced pressure and the residue was extracted with ethyl acetate. The ethyl acetate layer was washed with aqueous saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue was purified by chromatography on silica gel to obtain a solid. The solid was recrystallized from ethyl acetate to obtain 2-(6-bromo-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)-1,3-dithian-1-oxide (331 mg) (Compound 111).

Aufarbeitung

  1. distillationThe methanol was distilled off under reduced pressure
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with aqueous saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by chromatography on silica gel
  7. customto obtain a solid
  8. customThe solid was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5c9bd3735cca4502ad5129320f03ece5
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270308

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