Potassium Carbonate → HCID 23033053, compound

HRID 490230Notes

Reaction equation

HRID 490230 reaction equation
[CH3:1][NH:2][C:3](=[C:10]([C:13]#[N:14])[C:11]#[N:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>C(#N)C>[NH2:14][C:13]1[C:10]([C:11]#[N:12])=[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:2]([CH3:1])[C:22]=1[C:23]([O:25][CH3:26])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57674691HCID 57674691, compound

Product 1

HCID 23033053HCID 23033053, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

[(Methylamino)phenylmethylene]methane-1,1-dicarbonitrile (3.00 g) and anhydrous potassium carbonate (4.51 g) were added to acetonitrile (200 mL). A solution of methyl bromoacetate (3.09 mL) in acetonitrile (10 mL) was added thereto, and the mixture was heated to reflux for 3 hours. After cooling the mixture to room temperature, it was allowed to stand, the supernatant was separated by decantation, and the solvent was distilled off under reduced pressure. The concentrated residue was combined with the solid portion remaining after decantation, ethyl acetate and water were added, and extraction was performed 3 times with ethyl acetate. The organic layer was washed with water and saturated brine and then dried over anhydrous magnesium sulfate. After filtering off the magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized (hexane/ethyl acetate=1/1) to obtain the title compound (1.15 g) as a white solid. The recrystallized residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1→2/1) to obtain the title compound (1.21 g, (total of 2.36 g with the recrystallized portion), yield: 56%) as a white solid. The NMR and ESI/MS data for this compound are shown below.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customthe supernatant was separated by decantation
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionwere added
  6. extractionextraction
  7. washThe organic layer was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationAfter filtering off the magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was recrystallized (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-191aae9ef58a4496bc9facf4262bd8e9
Source dataset
uspto-grants-2009_05
Patent number
US07528140B2

Reaction notes

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