Ethyl Acetate → HCID 66968586, compound

HRID 2095860Notes

Reaction equation

HRID 2095860 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[CH:8]=1)=[O:5])#[N:2].CO/[CH:16]=[CH:17]/[C:18](=O)[CH3:19].N12CCN(CC1)CC2.C(OCC)(=O)C>COCCOCCO.O>[F:13][C:9]1[CH:8]=[C:7]([N:6]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:3]([C:1]#[N:2])[C:4]2=[O:5])[CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 9237DabcoHCID 639675(3E)-4-Methoxy-3-buten-2-oneHCID 9040122-Cyano-N-(3-fluorophenyl)acetamide

Product 1

HCID 66968586HCID 66968586, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8134Diethylene Glycol Monomethyl EtherSolvent

Procedure

A solution (50 mL) of 2-cyano-N-(3-fluorophenyl)acetamide (6.60 g, 37.0 mmol), (3E)-4-methoxybut-3-en-2-one (5.60 g, 56.0 mmol) and 1,4-diazabicyclo[2.2.2]octane (6.20 g, 56.0 mmol) in 2-(2-methoxyethoxy)ethanol was stirred at 120° C. for 12 hr. 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 (2.60 g, 31%) 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-b94f18400a114f34a0a32d980c602b2d
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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