Azidotrimethylsilane → 4,4-dimethyl-6-fluoro-8-nitro-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazine

HRID 1754411Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1754411
[F:1][C:2]1[C:7]2[O:8][C:9]([CH3:14])([CH3:13])[C:10](=S)[NH:11][C:6]=2[CH:5]=[C:4]([N+:15]([O-:17])=[O:16])[CH:3]=1.[Si]([N:22]=[N+:23]=[N-:24])(C)(C)C>C1COCC1.[Hg](OC(C)=O)OC(C)=O.CCOC(C)=O>[CH3:13][C:9]1([CH3:14])[O:8][C:7]2[C:2]([F:1])=[CH:3][C:4]([N+:15]([O-:17])=[O:16])=[CH:5][C:6]=2[N:11]2[N:22]=[N:23][N:24]=[C:10]12

Komponenten

6

Edukt 2

HCID 78378AzidotrimethylsilaneHCID 898638698-Fluoro-2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-thione

Produkt 1

HCID 904376754,4-dimethyl-6-fluoro-8-nitro-4H-benzo[b]tetrazolo[1,5-d][1,4]oxazineAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 16683746DiacetyloxymercuryLösungsmittel

Versuchsvorschrift

To a solution of 8-fluoro-2,2-dimethyl-6-nitro-2H-benzo[b][1,4]oxazin-3(4H)-thione (1.0 g, 3.9 mmol) in THF, Hg(OAc)2 was added at 0° C. TMS-N3 was added to the reaction mixture at 0° C. and stirred for 1 hour. Reaction mixture was allowed to warm to room temperature and stirred for 3 hours. LCMS analysis of the reaction mixture indicated completion of the reaction. After 3 hours, the reaction mixture was diluted with 100 ml of EtOAc and partitioned with saturated aqueous NH4Cl (100 ml). Layers were separated and the aqueous layer was washed twice with EtOAc (50 ml). Combined EtOAc layers were dried over Na2SO4 and concentrated. The crude product was purified by column chromatography to give the product in 57% yield (0.57 g). LCMS (m/z) 266 (MH+).

Aufarbeitung

  1. customReaction mixture
  2. stirringstirred for 3 hours
  3. customcompletion of the reaction
  4. waitAfter 3 hours
  5. custompartitioned with saturated aqueous NH4Cl (100 ml)
  6. customLayers were separated
  7. washthe aqueous layer was washed twice with EtOAc (50 ml)
  8. dry with materialCombined EtOAc layers were dried over Na2SO4
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography
  11. customto give the product in 57% yield (0.57 g)

Quellen und Nachweise

ORD-Eintrag
ord-64653c725c894a67bae572ca25eba64f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169249B2

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