Trifluoroacetic acid → 6-(2-Chloroethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1435865Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435865
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1)=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>CCOC(C)=O>[Cl:1][CH2:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][C:11](=[O:14])[NH:10][C:9]=2[CH:15]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 27644586-(2-chloroacetyl)-3,4-dihydro-2H-1,4-benzoxazin-3-one

Produkt 1

HCID 179831346-(2-Chloroethyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneAusbeute 95,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a dried flask under N2 atmosphere equipped with addition funnel was added 6-(2-chloroethanoyl)-4H-benzo[1,4]oxazin-3-one (10.0 g, 44.4 mmol) in trifluoroacetic acid (34 mL, 0.44 mol). To the resulting mixture at 0° C. was added triethylsilane (15.3 mL, 0.1 mole) dropwise over 5 min. The resulting mixture was warmed to 45° C. for 30 min and stirred at room temperature for 40 h. Reaction was poured onto ice water and layered with EtOAc. The organic layer was washed with water, brine, and dried over MgSO4. Solvent was removed on vacuum to give the desired compound as white solid (9.0 g, 93%). LC-MS (ES): m/e 212 (M+H)+.

Aufarbeitung

  1. customTo a dried flask under N2 atmosphere equipped with addition funnel
  2. customReaction
  3. additionwas poured onto ice water
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. customSolvent was removed on vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5c5f542d1cb34216a47e8ea4b0fc5335
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618959B2

Notizen zur Reaktion

Wird geladen…