(5-Phenyl-4H-1,2,4-triazol-3-yl)acetonitrile → 2-(3-phenyl-1H-1,2,4-triazol-5-yl)ethanamine

HRID 1397295ノート

反応式

HRID 1397295 の反応式
[C:1]1([C:7]2[N:11]=[C:10]([CH2:12][C:13]#[N:14])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[C:1]1([C:7]2[N:11]=[C:10]([CH2:12][CH2:13][NH2:14])[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

3

反応物 1

HCID 386778(5-Phenyl-4H-1,2,4-triazol-3-yl)acetonitrile

生成物 1

HCID 33324722-(3-phenyl-1H-1,2,4-triazol-5-yl)ethanamine収率 127.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Borane dimethyl sulfide complex (0.2 mL, 2.16 mmol) was added to a solution of compound 2-(3-phenyl-1H-1,2,4-triazol-5-yl)acetonitrile (100 mg, 0.54 mmol) in dry THF (5 mL) at room temperature. The reaction mixture was refluxed for 1 h, then quenched carefully with methanol and again heated to reflux for 0.5 h. The reaction mixture was concentrated under reduced pressure and then diluted with EtOAc. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 2-(3-phenyl-1H-1,2,4-triazol-5-yl)ethanamine (130 mg, crude), which was carried through without further purification. MS (ESI) m/z: Calculated for C10H12N4: 188.11. found: 189.2 (M+H)+.

後処理

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. customquenched carefully with methanol
  3. temperatureagain heated
  4. temperatureto reflux for 0.5 h
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additiondiluted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-297f471e35614cf799c3a75980510969
出典データセット
uspto-grants-2014_12
特許番号
US08901156B2

反応ノート

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