Dimethyl Sulfate → 2-Methoxy-4-methylbenzamide

HRID 1881802ノート

反応式

HRID 1881802 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 219473972-Methoxy-4-methylbenzamide収率 617.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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, 1H), 6.81 (d, J=7.6 Hz, 1H), 3.85 (s, 3H), 2.31 (s, 3H).

後処理

  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

出典と根拠

ORDレコード
ord-96db5cabd17044b9ace8936bd07f9758
出典データセット
uspto-grants-2012_11
特許番号
US08318947B2

反応ノート

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