(Dimethyl sulfide)trihydroboron → 4-methyl-7-methoxy-3,4-dihydro-2H-[1,4]benzoxazine

HRID 38414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 38414
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[N:7]([CH3:12])[C:8](=O)[CH2:9][O:10][C:5]=2[CH:4]=1.CSC.B>C1COCC1>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[N:7]([CH3:12])[CH2:8][CH2:9][O:10][C:5]=2[CH:4]=1

Komponenten

4

Edukt 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 233230137-Methoxy-4-methyl-4H-benzo[1,4]oxazin-3-one

Produkt 1

HCID 136712644-methyl-7-methoxy-3,4-dihydro-2H-[1,4]benzoxazineAusbeute 9,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7-Methoxy-4-methyl-4H-benzo[1,4]oxazin-3-one (13.07 g, 0.68 mol) was added to 100 mL dry THF, and the reaction mixture was refluxed under nitrogen. Borane-dimethyl sulfide (13.6 mL, 0.136 mol) was added dropwise over one hour, and the reaction mixture was allowed to reflux for two hours. The reaction mixture was cooled and then quenched by addition of 50 mL of 10% aqueous HCl. Precipitate was removed by filtration, and the liquid was concentrated under reduced pressure to give 11.17 g of 7-Methoxy-4-methyl-3,4-dihydro-2H-benzo[1,4]oxazine. (M+H)=180.

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed under nitrogen
  2. temperatureto reflux for two hours
  3. temperatureThe reaction mixture was cooled
  4. customquenched by addition of 50 mL of 10% aqueous HCl
  5. customPrecipitate was removed by filtration
  6. concentrationthe liquid was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c4c8b93db8174f0d9d32510454347528
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524725B2

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