Dimethyl Sulfide → 6-nitro-3,4-dihydro-2H-1,4-benzoxazine

HRID 401394

Reaktionsgleichung

Reaktionsgleichung von HRID 401394
S(C)C.[N+:4]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH2:14][C:13](=O)[NH:12][C:11]=2[CH:17]=1)([O-:6])=[O:5]>C1COCC1>[N+:4]([C:7]1[CH:8]=[CH:9][C:10]2[O:15][CH2:14][CH2:13][NH:12][C:11]=2[CH:17]=1)([O-:6])=[O:5]

Komponenten

4

Edukt 2

HCID 1068Dimethyl SulfideHCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-one

Produkt 1

HCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazineAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of BH3.Me2S in THF (2 M, 7.75 mL, 15.5 mmol) was added dropwise to a suspension of 6-nitro-4H-benzo[1,4]oxazin-3-one (0.6 g, 3.1 mmol) in THF (10 mL). The mixture was stirred at room temperature overnight. The reaction was quenched with MeOH (5 mL) at 0° C. and then water (20 mL) was added. The mixture was extracted with Et2O and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to give 6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine as a red solid (0.5 g, 89%), which was used without further purification.

Aufarbeitung

  1. customThe reaction was quenched with MeOH (5 mL) at 0° C.
  2. additionwater (20 mL) was added
  3. extractionThe mixture was extracted with Et2O
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-1dcdfc0ddf624765a8f910386261db07
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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