Ethylamine → (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide

HRID 749457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749457
[CH2:1]([NH2:3])[CH3:2].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([CH2:15][CH:16]=[CH2:17])[C:12](Cl)=[O:13])=[CH:7][CH:6]=1>C(Cl)Cl>[CH2:1]([NH:3][C:12](=[O:13])[C@H:11]([C:8]1[CH:7]=[CH:6][C:5]([F:4])=[CH:10][CH:9]=1)[CH2:15][CH:16]=[CH2:17])[CH3:2]

Komponenten

4

Edukt 2

HCID 6341EthylamineHCID 15536025(S)-2-(4-fluorophenyl)pent-4-enoyl chloride

Produkt 1

HCID 68978786(2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamideAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A stream of ethylamine was introduced to ice-cooled CH2Cl2 (5 mL) until 350 mg gas had been consumed. A solution of (2S)-2-(4-fluorophenyl)pent-4-enoyl chloride (0.24 g in 5 mL of CH2Cl2, 1.1 mmol) was added dropwise. The mixture was stirred at room temperature for 1 h and then diluted with CH2Cl2 (10 mL). The solution was washed with aqueous solutions of KHSO4 (8 mL, 1M), NaOH (8 mL, 1M) and then brine. The organic solution was dried over Na2SO4 and then the solvent was evaporated. There was obtained 0.15 g (59%) of (2S)-N-ethyl-2-(4-fluorophenyl)pent-4-enamide. 1H NMR (500 MHz, CDCl3): 1.1 (t, 3H), 2.5 (m, 1H), 2.8-3.0 (m, 2H), 3.2-3.4 (m, 3H), 5.0-5.1 (m, 2H), 5.6-5.8 (m, 1H), 7.0 (t, 2H), 7.3 (m, 2H).

Aufarbeitung

  1. customhad been consumed
  2. washThe solution was washed with aqueous solutions of KHSO4 (8 mL, 1M), NaOH (8 mL, 1M)
  3. dry with materialThe organic solution was dried over Na2SO4
  4. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-dbc78ff35b2941078b77e2bcd200f3c8
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402581B2

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