Iodoethane → 4-ethyl-3,4-dihydro-2H-benzo[1,4]oxazine

HRID 1695811

Reaktionsgleichung

Reaktionsgleichung von HRID 1695811
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH3:19]>CN(C=O)C>[CH2:18]([N:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:1][CH2:2][CH2:3]1)[CH3:19]

Komponenten

5

Edukt 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 5850963,4-Dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 129488774-ethyl-3,4-dihydro-2H-benzo[1,4]oxazineAusbeute 55,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of 3,4-dihydro-2H-benzo[1,4]oxazine (4.0 g, 29.6 mmol) in DMF (20 mL) was added potassium carbonate (10.22 g, 74.0 mmol). After stirring for five min. Iodo-ethane (3.5 mL, 44.4 mmol) was added and heated to 60° C. for overnight. Reaction mixture was cooled to room temperature, quenched by the addition of water (20 mL), extracted with ethyl acetate (3×25 mL). The organic layer was washed with water (30 mL), brine (30 mL), dried over sodium sulfate, concentrated and purified by silica gel column chromatoghraphy to furnish 4-ethyl-3,4-dihydro-2H-benzo[1,4]oxazine (2.7 g).

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. customquenched by the addition of water (20 mL)
  4. extractionextracted with ethyl acetate (3×25 mL)
  5. washThe organic layer was washed with water (30 mL), brine (30 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. custompurified by silica gel column chromatoghraphy

Quellen und Nachweise

ORD-Eintrag
ord-b0f9572da03a42c8b92730ba29882c00
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163704B2

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