Cesium carbonate → HCID 68846090, compound

HRID 490231Notes

Reaction equation

HRID 490231 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].CO[C:14](=[C:21]([C:24]#[N:25])[C:22]#[N:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:33][C:34]([O:36][CH3:37])=[O:35]>C(#N)C>[NH2:25][C:24]1[C:21]([C:22]#[N:23])=[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:1]([CH2:2][CH2:3][NH:4][C:5]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:11])[C:33]=1[C:34]([O:36][CH3:37])=[O:35]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 187201N-BOC-ethylenediamineHCID 726895HCID 726895, compound

Product 1

HCID 68846090HCID 68846090, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl N-(2-aminoethyl)carbamate (10.6 g) was added to a solution of (methoxyphenylmethylene)methane-1,1-dicarbonitrile (10.4 g) in acetonitrile (350 mL), and the mixture was stirred for 10 minutes. Anhydrous cesium carbonate (65.1 g) and methyl bromoacetate (13.5 mL) were added, and the mixture was heated to reflux for 1 hour. 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 purified by silica gel column chromatography (hexane/ethyl acetate 2/1) to obtain the title compound (20.6 g, yield: 95%) as a yellow transparent oil. The NMR and ESI/MS data for this compound-are shown below.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  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 purified by silica gel column chromatography (hexane/ethyl acetate 2/1)

Sources & evidence

ORD record
ord-105df2af60094a5d9f89052fb8fb2b8b
Source dataset
uspto-grants-2009_05
Patent number
US07528140B2

Reaction notes

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