Dimethyl Sulfate → 2-Methoxy-4-methylbenzamide

HRID 1518595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518595
[OH:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:12]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[CH3:12][O:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 105348392-Hydroxy-4-methylbenzamide

Produkt 1

HCID 219473972-Methoxy-4-methylbenzamideAusbeute 617,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-4-methyl-benzamide (15.1 g, 0.1 mol) and K2CO3 (41.7 g, 0.3 mol) in 1000 mL of acetone was heated to reflux for 1 hour before Me2SO4 was added at that temperature. The resulting mixture was refluxed overnight. The reaction mixture was then filtered and the filtrate was concentrated. The resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1) and stirred at room temperature for 3 hours. After removal of the solvent, the residue was recrystallized from EtOAc/PE to afford 102 g of 2-methoxy-4-methyl-benzamide (yield 61%). 1H NMR (400 MHz, DMSO-d6): δ 7.72 (d, J=7.6 Hz, 1H), 7.57 (br s, 1H), 7.46 (br s, 1H), 6.92 (s, 1 H), 6.81 (d, J=7.6 Hz, 1 H), 3.85 (s, 3H), 2.31 (s, 3H).

Aufarbeitung

  1. temperaturewas heated
  2. additionwas added at that temperature
  3. temperatureThe resulting mixture was refluxed overnight
  4. filtrationThe reaction mixture was then filtered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe resulting residue was dissolved in 1000 mL of methanol/ammonia (1:1)
  7. customAfter removal of the solvent
  8. customthe residue was recrystallized from EtOAc/PE

Quellen und Nachweise

ORD-Eintrag
ord-f5c24dac11c6453ca71999cdc77cb7c5
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09072313B2

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