Dimethyl Sulfate → 2-Methoxy-4-methylbenzamide

HRID 1686128노트

반응식

HRID 1686128 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 219473972-Methoxy-4-methylbenzamide수율 617.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-37bdb46a126e4e1bb06697c987aaa806
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08148536B2

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