Methyl iodide → 3-Acetyl-4-methoxyacetanilide

HRID 1870230노트

반응식

HRID 1870230 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 28174183-Acetyl-4-methoxyacetanilide수율 100%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-968a67cf23a345b4b7bec1c6c7034b40
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06096766

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