Chloroacetyl chloride → 6-Nitro-2H-1,4-benzoxazin-3(4H)-one

HRID 74061

Reaktionsgleichung

Reaktionsgleichung von HRID 74061
Cl[CH2:2][C:3](Cl)=[O:4].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([NH2:16])[CH:10]=1)([O-:8])=[O:7].C([O-])(O)=O.[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(Cl)(Cl)Cl>[N+:6]([C:9]1[CH:14]=[CH:13][C:12]2[O:15][CH2:2][C:3](=[O:4])[NH:16][C:11]=2[CH:10]=1)([O-:8])=[O:7]

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 36133892-Amino-4-Nitrophenol

Produkt 1

HCID 27636836-Nitro-2H-1,4-benzoxazin-3(4H)-oneAusbeute 41,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5963Benzyltrimethylammonium chlorideKatalysatorHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

At 0° C., chloroacetyl chloride (8.75 mL, 0.11 mol) was added dropwise to a mixture of 4-nitro-2-aminophenol (15.4 g, 0.1 mol), benzyltrimethylammonium chloride (18.6 g, 0.1 mol) and NaHCO3 (42 g, 0.5 mol) in chloroform (350 ml) over a period of 30 min. After addition, the reaction mixture was stirred at 0° C. for 1 h, then at 50° C. overnight. The solvent was removed under reduced pressure and the residue was treated with water (50 ml). The solid was collected via filtration, washed with water and recrystallized from ethanol to provide 6-nitro-4H-benzo[1,4]oxazin-3-one as a pale yellow solid (8 g, 41%).

Aufarbeitung

  1. additionAfter addition
  2. customat 50° C.
  3. customovernight
  4. customThe solvent was removed under reduced pressure
  5. additionthe residue was treated with water (50 ml)
  6. filtrationThe solid was collected via filtration
  7. washwashed with water
  8. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-40ba61ee9c604417a896c4992bf6d27b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829204B2

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