Triethylamine → Methyl 4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-ylmethyl)-benzoate

HRID 252765

Reaktionsgleichung

Reaktionsgleichung von HRID 252765
CCN(CC)CC.[O:8]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10](=[O:18])[CH2:9]1.[CH:19]([C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1)=O>CC(OC(C)=O)=O>[O:18]=[C:10]1[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:8][CH:9]1[CH2:19][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][CH:22]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 15294Methyl 4-FormylbenzoateHCID 727572H-1,4-benzoxazin-3(4H)-one

Produkt 1

HCID 22478824Methyl 4-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-2-ylmethyl)-benzoateAusbeute 13,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Et3N (3.18 ml, 22.8 mmol) was added to a stirring solution of 2-H-1,4-benzoxazin-3-(4H)one (2.50 g, 16.8 mmol) and methyl 4-formylbenzoate (4.59 g, 27.5 mmol) in Ac2O (20 ml). The reaction mixture was refluxed 16 h. After this mixture was cooled for 3 days, the solid was filtered and rinsed with ethyl acetate to afford the title compound 266 (657 mg, 13%) as a yellow solid. LRMS: 295.1 (Calc.); 296.0 (found).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed 16 h
  2. temperatureAfter this mixture was cooled for 3 days
  3. filtrationthe solid was filtered
  4. washrinsed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-48e40678d999481296aeb53e63e83884
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868204B2

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