Triphenylphosphine → 2-(3-Nitrophenyl)ethan-1-amine

HRID 1597146ノート

反応式

HRID 1597146 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH2:7][CH2:8][N:9]=[N+]=[N-])([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[CH2:7][CH2:8][NH2:9])([O-:3])=[O:2]

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 224575343-Nitrophenethyl azide

生成物 1

HCID 129500662-(3-Nitrophenyl)ethan-1-amine収率 80.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-nitrophenethyl azide (0.9 g, 4.69 mmol), triphenyl phosphine (1.22 g, 4.66 mmol) and CH2Cl2 (80 mL) is stirred at room temperature for 3 days. Solvent is removed and the residue is taken up in EtOH (20 mL). The solution is heated to 70° C., added 2M NaOH aqueous solution (10 mL) and stirred at room temperature for 2 hrs. A 10% HCl aqueous solution (20 mL) is then added and refluxed for 2 hrs. After the mixture cool to room temperature, it is washed with benzene, basified with 5N NaOH to pH˜12, extracted with ethyl acetate. The organic layer is dried over Na2SO4 and concentrated to give the product (0.63 g) as a yellow oil.

後処理

  1. customSolvent is removed
  2. temperatureThe solution is heated to 70° C.
  3. additionadded 2M NaOH aqueous solution (10 mL)
  4. stirringstirred at room temperature for 2 hrs
  5. additionA 10% HCl aqueous solution (20 mL) is then added
  6. temperaturerefluxed for 2 hrs
  7. temperatureAfter the mixture cool to room temperature
  8. washit is washed with benzene
  9. extractionextracted with ethyl acetate
  10. dry with materialThe organic layer is dried over Na2SO4
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-ec5f274b9a754f74a9ae132f48149ec3
出典データセット
uspto-grants-2001_09
特許番号
US06294529B1

反応ノート

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