Acetyl chloride → 1-(6-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone

HRID 74063

Reaktionsgleichung

Reaktionsgleichung von HRID 74063
[C:1](Cl)(=[O:3])[CH3:2].[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[O:16][CH2:15][CH2:14][NH:13][C:12]=2[CH:17]=1)([O-:7])=[O:6].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([N:13]1[C:12]2[CH:17]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=[CH:10][C:11]=2[O:16][CH2:15][CH2:14]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 70622256-nitro-3,4-dihydro-2H-1,4-benzoxazine

Produkt 1

HCID 578647141-(6-nitro-2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanoneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Under vigorous stirring at room temperature, acetyl chloride (1.02 g, 13 mmol) was added dropwise to a mixture of 6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine (1.8 g, 10 mmol) and NaHCO3 (7.14 g, 85 mmol) in CH2Cl2 (50 mL). After addition, the reaction was stirred for 1 h at this temperature. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was treated with Et2O:hexane (1:2, 50 mL) under stirring for 30 min and then filtered to give 4-acetyl-6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine as a pale yellow solid (2 g, 90%).

Aufarbeitung

  1. additionAfter addition
  2. stirringthe reaction was stirred for 1 h at this temperature
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. additionThe residue was treated with Et2O:hexane (1:2, 50 mL)
  6. stirringunder stirring for 30 min
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-7ccda5df6a2047b99cc019ca9cb59536
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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