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

HRID 427653ノート

反応式

HRID 427653 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 478806N-(4-Methoxyphenyl)-2-hydroxybenzamide収率 80.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a158a20cb9ef4a178bc3bc046c3a1591
出典データセット
uspto-grants-2001_11
特許番号
US06313122B1

反応ノート

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