Sodium Iodide → HCID 14763125, Verbindung

HRID 275130

Reaktionsgleichung

Reaktionsgleichung von HRID 275130
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:13]=1)([O-:3])=[O:2].Br[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:27][O:26][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:16]=1[CH2:15][N:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=2[O:12][CH2:11][CH2:10]1)[C:20]([O:22][CH3:23])=[O:21]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 14763125HCID 14763125, VerbindungAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 6-nitro-2,3-dihydrobenz-1,4-oxazine (0.45 g.), methyl 4-bromomethyl-3-methoxybenzoate (B) (0.65 g.), anhydrous potassium carbonate (0.35 g.), sodium iodide (0.38 g.) and acetone (25 ml.) was stirred and heated under reflux for 48 hours, under an atmosphere of nitrogen. The cooled reaction mixture was separated by filtration. The residue was washed with acetone, and the filtrate and washings were evaporated. The resulting solid was dissolved in dichloromethane and residual solid removed by filtration. The filtrate was evaporated. The product was purified by flash chromatography on silica gel (3 cm. diameter column), eluting with 1:10 v/v ethyl acetate: toluene, to give methyl 3-methoxy-4-(6-nitro-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl)benzoate (G) (0.75 g., 84%), m.p. 130°-132° C.; NMR (80 MHz, CDCl3): 3.0(t,2H, OCH2.CH2N), 3.8(s,3H, OCH3), 3.95(s,3H, OCH3), 4.3(t, 2H, OCH2.CH2N), 4.5(s,2H, CH2.Ar), 6.8(d,1H), 7.5(m, 5H).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 48 hours, under an atmosphere of nitrogen
  3. customThe cooled reaction mixture
  4. customwas separated by filtration
  5. washThe residue was washed with acetone
  6. customthe filtrate and washings were evaporated
  7. dissolutionThe resulting solid was dissolved in dichloromethane
  8. customresidual solid removed by filtration
  9. customThe filtrate was evaporated
  10. customThe product was purified by flash chromatography on silica gel (3 cm. diameter column)
  11. washeluting with 1:10 v/v ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-62eea3f9fbb947429f40dbed005140ca
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05391758

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