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

HRID 1397295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1397295
[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

Komponenten

3

Edukt 1

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

Produkt 1

HCID 33324722-(3-phenyl-1H-1,2,4-triazol-5-yl)ethanamineAusbeute 127,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-297f471e35614cf799c3a75980510969
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08901156B2

Notizen zur Reaktion

Wird geladen…