Chlorotrimethylsilane → 2-(4-(N-salicyloyl)aminophenyl)propionic acid

HRID 479017

反応式

HRID 479017 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.C[Si](Cl)(C)C.C(N(CC)CC)C.CC([O:28][C:29]1[C:34]([C:35](Cl)=[O:36])=[CH:33][CH:32]=[CH:31][CH:30]=1)=O>C(Cl)Cl>[C:35]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)(=[O:36])[C:34]1[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=1)[OH:28]

参加物

6

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 430264-Aminohydratropic acidHCID 796682-Acetoxybenzoyl chloride

生成物 1

HCID 98173032-(4-(N-salicyloyl)aminophenyl)propionic acid収率 52.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A slurry of 58.6 g (0.355 mol) of 2-(4-aminophenyl)propionicacid and 500 ml of methylene chloride was treated with 90.11 ml (77.13 g, 0-710 mol) of trimethylsilyl chloride and was heated to reflux for 120 min. The reaction mixture was cooled to 0° C. and treated with 184.44 ml (107.77 g, 1.065 mol) of triethylamine. After stirring for 5 minutes, this mixture was treated with a solution of 70.45 g (0.355 mol) of O-acetylsalicyloyl chloride and 150 ml of methylene chloride. The reaction mixture was warmed to 25° C. and stirred for 64 hr. The volatiles were removed in vacuo. The residue was stirred in 2N aqueous sodium hydroxide for one hour and acidified with 2 M aqueous sulfuric acid. The solid was recrystallized twice from ethanol/water to give a tan solid. Isolation by filtration afforded 53.05 g of (52% yield) of 2-(4-(N-salicyloyl)aminophenyl)propionic acid.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 120 min
  3. temperatureThe reaction mixture was warmed to 25° C.
  4. stirringstirred for 64 hr
  5. customThe volatiles were removed in vacuo
  6. stirringThe residue was stirred in 2N aqueous sodium hydroxide for one hour
  7. customThe solid was recrystallized twice from ethanol/water
  8. customto give a tan solid
  9. filtrationIsolation by filtration

出典と根拠

ORDレコード
ord-1ae6f0b86b0f4478bba672050e38a6c8
出典データセット
uspto-grants-2003_11
特許番号
US06642411B1

関連ノート

読み込み中…