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

HRID 1449854Notes

Reaction equation

HRID 1449854 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-e321af82e9594e42820010316f48752b
Source dataset
uspto-grants-1997_02
Patent number
US05599986

Reaction notes

Loading…