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

HRID 749457노트

반응식

HRID 749457 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dbc78ff35b2941078b77e2bcd200f3c8
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402581B2

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