Acetyl chloride → N1-[5-Acetyl-3-(tert-butyl)-2-(methoxymethoxy)phenyl]acetamide

HRID 1295995ノート

反応式

HRID 1295995 の反応式
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[C:11]([C:23](=[O:25])[CH3:24])[CH:12]=[C:13]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:14]=1[O:15][CH2:16][O:17][CH3:18].[C:26](Cl)(=[O:28])[CH3:27]>O1CCCC1>[C:23]([C:11]1[CH:12]=[C:13]([C:19]([CH3:20])([CH3:21])[CH3:22])[C:14]([O:15][CH2:16][O:17][CH3:18])=[C:9]([NH:8][C:26](=[O:28])[CH3:27])[CH:10]=1)(=[O:25])[CH3:24]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 229296651-[3-Amino-5-(tert-butyl)-4-(methoxymethoxy)phenyl]-1-ethanone

生成物 1

HCID 58910001N1-[5-Acetyl-3-(tert-butyl)-2-(methoxymethoxy)phenyl]acetamide収率 89.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triethylamine (60 ml, 430 mmol) was added to a solution of the 1-[3-amino-5-(tert-butyl)-4-(methoxymethoxy)phenyl]-1-ethanone (53.9 g, 215 mmol) in tetrahydrofuran (270 ml) while cooling on ice under a nitrogen atmosphere and then acetyl chloride (23 ml, 323 mmol) was added dropwise. After stirring at the same temperature for 10 minutes, the mixture was stirred at room temperature for 30 minutes. The solvent was distilled off under reduced pressure, water was added to the residue and then extraction was performed with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid water, water, saturated aqueous sodium hydrogencarbonate and brine in that order. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to yield the title compound (56.2 g, 89.3% yield) as light brown needle-like crystals.

後処理

  1. temperaturewhile cooling on ice under a nitrogen atmosphere
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. distillationThe solvent was distilled off under reduced pressure, water
  4. additionwas added to the residue
  5. extractionextraction
  6. washThe organic layer was washed with 1 N hydrochloric acid water, water, saturated aqueous sodium hydrogencarbonate and brine in that order
  7. dry with materialAfter drying with anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-fc1c41706a834d2ba23469283b945d3d
出典データセット
uspto-grants-2007_07
特許番号
US07244730B2

反応ノート

読み込み中…