Salicylic Acid → N-(4-Methoxyphenyl)-2-hydroxybenzamide

HRID 395803

반응식

HRID 395803 반응식
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(Cl)(=O)C(Cl)=O.C([N:19]([CH2:22][CH3:23])CC)C.C(Cl)(=O)C1C=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1>C(Cl)Cl.CN(C)C=O>[CH3:32][O:31][C:28]1[CH:29]=[CH:23][C:22]([NH:19][C:1](=[O:10])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[OH:4])=[CH:26][CH:27]=1

참가 물질

7

반응물 4

HCID 338Salicylic AcidHCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 65578Oxalyl chloride

생성물 1

HCID 478806N-(4-Methoxyphenyl)-2-hydroxybenzamide수율 80.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매2회

실험 절차

To a solution of salicylic acid (1.38 g, 10.0 mmol) in methylene chloride (100 mL) cooled to 0° C. was added a few drops of dry N,N-dimethylformamide, followed by oxalyl chloride (1.41 mL). After 39 min, the ice bath was removed, and the reaction mixture allowed to warm to room temperature over 2 h. The solvent was removed in vacuo, and the residue dissolved in dry methylene chloride (125 mL). After cooling the solution to 0° C., triethylamine (2.81 mL, 20.0 mmol) was added, followed by the dropwise addition of a solution of p-anisoyl chloride (2.46 g, 20.0 mmol) in methylene chloride (25 mL). After 1 h, the reaction mixture was washed twice with 1 N aqueous hydrochloric acid and once with cold saturated aqueous sodium bicarbonate solution. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. Trituration with hexane, produced 1.95 g (80%) of the title compound as a crystalline solid.

후처리

  1. customthe ice bath was removed
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in dry methylene chloride (125 mL)
  4. temperatureAfter cooling the solution to 0° C.
  5. waitAfter 1 h
  6. washthe reaction mixture was washed twice with 1 N aqueous hydrochloric acid and once with cold saturated aqueous sodium bicarbonate solution
  7. dry with materialThe organic layer was dried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3c4cee2b060a4d15a828452652d776c7
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605626B2

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