Sodium hydride → (5-Nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanol

HRID 896008

Reaktionsgleichung

Reaktionsgleichung von HRID 896008
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH:12]2[CH2:14][O:13]2)[C:5]=1[NH2:15])([O-:3])=[O:2].[H-].[Na+]>CN(C=O)C>[N+:1]([C:4]1[C:5]2[NH:15][CH:12]([CH2:14][OH:13])[CH2:11][O:10][C:6]=2[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 113448381-(2-Amino-3-nitrophenoxy)-2,3-epoxypropane

Produkt 1

HCID 22349487(5-Nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanolAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-nitro-6-oxiranylmethoxy-phenylamine (14.7 g, 0.070 mol) in DMF (200 mL) was added sodium hydride (3.5 g, 60 wt. %, 0.087 mol). The resulting reaction mixture was stirred at room temperature overnight. The mixture was evaporated in vacuum, the residue diluted with water (200 mL) and extracted with methylene chloride (2×200 mL). The combined organic layers were washed with water (300 mL) and saturated sodium chloride solution (300 mL), dried (Na2SO4) and concentrated to provide the title compound as a dark red crystal (11.0 g). 1H NMR (DMSO-d6): δ 8.30 (d, 1H); 7.60 (dd, 1H); 7.00 (dd, 1H); 6.65 (dd, 1H); 5.15 (t, 1H); 4.10 (m, 2H); 3.70 (m, 1H); 3.50 (m, 2H).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. customThe mixture was evaporated in vacuum
  3. additionthe residue diluted with water (200 mL)
  4. extractionextracted with methylene chloride (2×200 mL)
  5. washThe combined organic layers were washed with water (300 mL) and saturated sodium chloride solution (300 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-35f1276ba2874e849f0808c0c0954568
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919334B2

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