Triethylamine → 7-Allyl-6-methoxy-1,4-dihydrobenz[d][1,3]oxazin-2-one

HRID 494949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494949
[NH2:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]=[CH2:12])[C:7]([O:13][CH3:14])=[CH:6][C:3]=1[CH2:4][OH:5].Cl[C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.O.N>O1CCCC1.O>[CH2:10]([C:8]1[C:7]([O:13][CH3:14])=[CH:6][C:3]2[CH2:4][O:5][C:16](=[O:18])[NH:1][C:2]=2[CH:9]=1)[CH:11]=[CH2:12]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 12896473Azane;hydrateHCID 576828172-Amino-5-methoxy-4-(2-propenyl)benzylalcohol

Produkt 1

HCID 576828047-Allyl-6-methoxy-1,4-dihydrobenz[d][1,3]oxazin-2-oneAusbeute 126,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

677 mg of 2-amino-5-methoxy-4-(2-propenyl)benzylalcohol was dissolved in 20 ml of tetrahydrofuran under nitrogen atmosphere. Thereafter, 0.52 g of triphosgene and 1.46 ml of triethylamine were added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, while cooling on ice, water and ammonia water were added to the reaction solution until foaming was terminated. The reaction solution was diluted with ethyl acetate and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) and then reprecipitated from ethyl acetate, so as to obtain 485 mg of the subject compound.

Aufarbeitung

  1. temperaturewhile cooling on ice
  2. additionwere added to the reaction solution until foaming
  3. customwas terminated
  4. additionThe reaction solution was diluted with ethyl acetate
  5. washwashed with water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)
  9. customreprecipitated from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fef5dadcdca042ddac5384dd06508fa4
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538123B2

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