Methyl iodide → 3-Acetyl-4-methoxyacetanilide

HRID 1870230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870230
CI.[C:3]([C:6]1[CH:7]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][C:11]=1[OH:12])(=[O:5])[CH3:4].[C:17](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:3]([C:6]1[CH:7]=[C:8]([NH:13][C:14](=[O:16])[CH3:15])[CH:9]=[CH:10][C:11]=1[O:12][CH3:17])(=[O:5])[CH3:4]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 81720N-(3-Acetyl-4-hydroxyphenyl)acetamide

Produkt 1

HCID 28174183-Acetyl-4-methoxyacetanilideAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl iodide (3.42 ml, 7.81 g, 55 mmol) was added to a stirred mixture of N-(3-acetyl-4-hydroxyphenyl)acetamide (J.Org.Chem. 1995, 60, 4324-4330) (9.65 g, 50 mmol) and potassium carbonate (13.82 g, 100 mmol) in dimethylformamide (50 ml). The mixture was stirred at room temperature for 72 hours, then the solvent was evaporated under reduced pressure. Water (100 ml) was added and the mixture was extracted with ethyl acetate (6×100 ml). The combined organic fractions were dried (MgSO4) and evaporated under reduced pressure to give N-(3-acetyl-4-methoxyphenyl)acetamide as a tan solid (10.34 g, 100%), 1H NMR (d6 -DMSO) δ 9.91 (1H, br. s), 7.76 (2H, m), 7.12 (1H, d, J=9.6 Hz), 3.86 (3H, s), 2.52 (3H, s), and 2.01 (3H, s). m/e (CI+) 208 (MH+).

Aufarbeitung

  1. customthe solvent was evaporated under reduced pressure
  2. additionWater (100 ml) was added
  3. extractionthe mixture was extracted with ethyl acetate (6×100 ml)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-968a67cf23a345b4b7bec1c6c7034b40
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06096766

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