1H-1,2,4-Triazole → (S)-1-(3-[1,2,4]triazol-1-yl-phenyl)-ethylamine

HRID 720262ノート

反応式

HRID 720262 の反応式
Br[C:2]1[CH:3]=[C:4]([C@@H:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[NH:11]1[CH:15]=[N:14][CH:13]=[N:12]1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cu]I>[N:11]1([C:2]2[CH:3]=[C:4]([C@@H:8]([NH2:10])[CH3:9])[CH:5]=[CH:6][CH:7]=2)[CH:15]=[N:14][CH:13]=[N:12]1

参加物

6

反応物 3

HCID 92571H-1,2,4-TriazoleHCID 11430Potassium CarbonateHCID 9952938(S)-1-(3-bromophenyl)ethanamine

生成物 1

HCID 11229236(S)-1-(3-[1,2,4]triazol-1-yl-phenyl)-ethylamine収率 36%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
195 °C

実験手順

To a solution of (S)-1-(3-bromo-phenyl)-ethylamine (1.5 g, 7.5 mmol) and 1,2,4-triazole (1.04 g, 15 mmol) in N-methylpyrrolidinone (10 mL) in a quartz tube were added potassium carbonate (2.1 g, 15 mmol) and copper (1) iodide (143 mg, 0.75 mmol). The reaction mixture was heated at 195° C. for 5 h in a Mars 5 microwave oven (600 W), cooled down to room temperature and filtered. The crude product was purified by flash chromatography (10% MeOH/89% EtOAC/1% triethylamine) to provide the title compound (504 mg, 36% yield) as a brown oil.

後処理

  1. temperaturecooled down to room temperature
  2. filtrationfiltered
  3. customThe crude product was purified by flash chromatography (10% MeOH/89% EtOAC/1% triethylamine)

出典と根拠

ORDレコード
ord-82886181818f474ba7d39448cc9df63b
出典データセット
uspto-grants-2006_11
特許番号
US07135472B2

反応ノート

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