Dimethylformamide → (E)-N-(2-(fluoromethylene)-4-(p-fluorophenyl)butyl)-N-formyl formamide

HRID 1449854노트

반응식

HRID 1449854 반응식
[CH:1]([N-:3][CH:4]=[O:5])=[O:2].[Na+].C(#N)C.CN(C)C=O.Cl[CH2:16]/[C:17](=[CH:27]/[F:28])/[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1>O>[F:28]/[CH:27]=[C:17](\[CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)/[CH2:16][N:3]([CH:4]=[O:5])[CH:1]=[O:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 9815806(E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butaneHCID 10877056Sodium Diformylamide

생성물 1

HCID 15342055(E)-N-(2-(fluoromethylene)-4-(p-fluorophenyl)butyl)-N-formyl formamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Combine sodium diformylamide (28.8 g, 0.31 mol), acetonitrile (360 g), and N,N-dimethylformamide (48 g). Add (E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butane (50.6 g, 0.23 mol). Heat to reflux. After 5 hours, cool to ambient temperature. Add water (466 g) and stir for 15 minutes. After 30 minutes, the aqueous layer is removed. Evaporate the organic layer in vacuo to give the title compound. 1H NMR (CDCl3, 300 MHz) δ 2.28 (m, 2H), 2.72 (m, 2H), 4.07 (d, J=3 Hz, 2H), 6.74 (d, J=81 Hz, 1H), 6.94 (m, 2H), 7.13 (m, 2H), 8.73 (s, 2H).

후처리

  1. temperatureHeat to reflux
  2. waitAfter 30 minutes
  3. customthe aqueous layer is removed
  4. customEvaporate the organic layer in vacuo

출처 및 근거

ORD 기록
ord-e321af82e9594e42820010316f48752b
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05599986

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