Ethyl Acetate → HCID 66968831, compound

HRID 2095864Notes

Reaction equation

HRID 2095864 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[C:9]([F:14])[CH:8]=1)=[O:5])#[N:2].CO/[CH:17]=[CH:18]/[C:19](=O)[CH3:20].N12CCN(CC1)CC2.C(OCC)(=O)C>COCCOCCO.O>[F:14][C:9]1[CH:8]=[C:7]([N:6]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:3]([C:1]#[N:2])[C:4]2=[O:5])[CH:12]=[C:11]([F:13])[CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9237DabcoHCID 639675(3E)-4-Methoxy-3-buten-2-oneHCID 16077530HCID 16077530, compound

Product 1

HCID 66968831HCID 66968831, compoundYield 40.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

A solution (30 mL) of 2-cyano-N-(3,5-difluorophenyl)acetamide (3.10 g, 16.0 mmol), (3E)-4-methoxybut-3-en-2-one (2.40 g, 24.0 mmol) and 1,4-diazabicyclo[2.2.2]octane (2.70 g, 24.0 mmol) in 2-(2-methoxyethoxy)ethanol was stirred at 130° C. for 12 hr. After cooling to room temperature, the reaction solution was divided into two layers with ethyl acetate and water and subjected to extraction (3 times) with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate and collected by filtration to give the title compound (1.60 g, 40%) as a brown solid.

Workup

  1. extractionsubjected to extraction (3 times) with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated under reduced pressure
  6. washthe obtained residue was washed with ethyl acetate
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-37c2b7c6921e474b90c0da4cf39cc740
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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