Methyl iodide → 6-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1045363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1045363
[C:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)(=[O:3])[CH3:2].CI.[C:17](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[N:11]([CH3:17])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 36419566-Acetyl-2H-1,4-benzoxazin-3(4H)-one

Produkt 1

HCID 405391446-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-oneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Acetyl-2H-benzo[b][1,4]oxazin-3(4H)-one (1 g, 5.23 mmol), methyl iodide (1.13 g, 7.84 mmol) and cesium carbonate (2.55 g, 7.84 mmol) were dissolved in DMF (2 mL). The reaction mixture was irradiated by microwave for 30 minutes at 100° C. The solvent was removed and extracted with dichloromethane. Purification by silica chromatography (ISCO) produced 6-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one (0.9 g, 84%). 1H NMR (400 MHz, CDCl3): δ 7.63 (s, 1H), 7.60 (d, 1H), 7.01 (d, 1H), 4.70 (s, 2H), 3.42 (s, 3H), 2.60 (s, 3H); MS (ESI) m/z: Calculated for C11H11NO3: 205.1. found: 206.1 (M+H)+.

Aufarbeitung

  1. customThe reaction mixture was irradiated by microwave for 30 minutes at 100° C
  2. customThe solvent was removed
  3. extractionextracted with dichloromethane
  4. customPurification by silica chromatography (ISCO)

Quellen und Nachweise

ORD-Eintrag
ord-7ab2d9a2963343aabcc2a81190f2ca72
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569282B2

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