Water → HCID 19073539, compound

HRID 1955988Notes

Reaction equation

HRID 1955988 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH:6]([N:9]([CH:16]([CH3:18])[CH3:17])[C:10](=O)[C:11]([F:14])([F:13])[F:12])[C:7]#N)=[CH:4][CH:3]=1.ClC(=C)[C:23]#[N:24].[C:26](OCC)(=O)C.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]2[N:9]([CH:16]([CH3:17])[CH3:18])[C:10]([C:11]([F:12])([F:13])[F:14])=[CH:26][C:7]=2[C:23]#[N:24])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 701982-ChloroacrylonitrileHCID 10935622HCID 10935622, compound

Product 1

HCID 19073539HCID 19073539, compoundYield 20.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of N-(p-chloro-α-cyanobenzyl)-2,2,2-trifluoro-N-isopropylacetamide (6.1 g, 0.02 mol) in toluene is treated at room temperature with tetrafluoroboric acid diethyl etherate (4.2 g as is, 3.6 g real, 0.022 mol) under a nitrogen atmosphere, heated to 60° C., treated with 2-chloroacrylonitrile (2.62 g, 0.03 mol) over 15-20 minutes, held at 60° C. for 3 hours, cooled to room temperature and treated with ethyl acetate and water. The phases are separated and the organic phase is washed with water and concentrated to give a brown gum residue. Flash column chromatography of the residue on silica gel packed and eluted with 15% ethyl acetate in heptane gives the title product as a brown oil, 1.3 g (20.8% yield), identified by 1H and 19F NMR and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. customThe phases are separated
  3. washthe organic phase is washed with water
  4. concentrationconcentrated
  5. customto give a brown gum residue
  6. washeluted with 15% ethyl acetate in heptane

Sources & evidence

ORD record
ord-d04f5fd093914a2387142e8333345331
Source dataset
uspto-grants-1998_07
Patent number
US05777132

Reaction notes

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