Triethylamine → 3-(2-Fluorobenzoyl)amino-epsilon-caprolactam

HRID 1463468ノート

反応式

HRID 1463468 の反応式
[NH2:1][CH:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1.C(N(CC)CC)C.[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21]>C(Cl)Cl>[F:17][C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH:1][CH:2]1[CH2:9][CH2:8][CH2:7][NH:6][C:4](=[O:5])[CH2:3]1)=[O:21]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 215841384-Aminoazepan-2-one

生成物 1

HCID 190904013-(2-Fluorobenzoyl)amino-epsilon-caprolactam

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3-Amino-ε-caprolactam (11.0 g) and triethylamine (15.7 ml) were added to 200 ml of methylenechloride. Then a solution of 2-fluorobenzoyl chloride (15.0 g) in methylenechloride (30 ml) was added dropwise to the mixture under ice-cooling and stirring. Thereafter, the mixture was stirred for 1.5 hrs. at room temperature, and the resultant precipitate was collected by filtration to give 3-(2-fluorobenzoyl)amino-ε-caprolactam as crude crystals. This crystals and phosphorus pentasulfide (16.5 g) were added to 200 ml of pyridine, and the whole was refluxed for 12 hrs. After cooling, the pyridine was removed by distillation, and to the residue was added a saturated sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with water, dried, and the solvent was distilled off under reduced pressure. The residue was purified by a column chromatography on silica gel, and then recrystallized from ethyl ether to give the title compound (4.55 g, 24.7%).

後処理

  1. temperaturecooling
  2. stirringThereafter, the mixture was stirred for 1.5 hrs
  3. filtrationat room temperature, and the resultant precipitate was collected by filtration

出典と根拠

ORDレコード
ord-9f8a579b6843469f91f986204b7f4374
出典データセット
uspto-grants-1994_04
特許番号
US05300639

反応ノート

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