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

HRID 74062

Reaktionsgleichung

Reaktionsgleichung von HRID 74062
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-c6aa03eb385c434599bcefdaaac81f0c
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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