Dabco → HCID 66968917, compound

HRID 2095776Notes

Reaction equation

HRID 2095776 reaction equation
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[CH3:14])=[O:5])#[N:2].CO[CH:17]=[CH:18][C:19](=O)[CH3:20].N12CCN(CC1)CC2>COCCOCCO.C(OCC)(=O)C>[F:13][C:10]1[CH:11]=[CH:12][C:7]([N:6]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:3]([C:1]#[N:2])[C:4]2=[O:5])=[C:8]([CH3:14])[CH:9]=1

Participants

6

Reactant 3

HCID 9237DabcoHCID 942973-Buten-2-one, 4-methoxy-HCID 16077534HCID 16077534, compound

Product 1

HCID 66968917HCID 66968917, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 8134Diethylene Glycol Monomethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

2-Cyano-N-(4-fluoro-2-methylphenyl)acetamide (2.0 g, 10 mmol) and 4-methoxybut-3-en-2-one (1.4 mL, 13 mmol) were suspended in 2-(2-methoxyethoxy)ethanol (20 mL), and 1,4-diazabicyclo[2.2.2]octane (1.2 g, 10 mmol) was added. The mixture was stirred at 120° C. for 6 hr, and cooled to room temperature. The mixture was diluted with ethyl acetate (40 mL), and washed with saturated aqueous sodium hydrogen carbonate solution. Then the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. Hexane-ethyl acetate was added to the residue, and the resulting precipitate was collected by filtration to give the title compound (630 mg, 25%) as a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. washwashed with saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThen the organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionHexane-ethyl acetate was added to the residue
  6. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-2583797d4ef74a658410a09c18f52973
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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