Cesium carbonate → HCID 23033050, compound

HRID 490233Notes

Reaction equation

HRID 490233 reaction equation
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.[CH:10]([O:13][CH2:14][CH2:15][CH2:16][NH2:17])([CH3:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27]>C(#N)C>[NH2:9][C:8]1[C:5]([C:6]#[N:7])=[CH:4][N:17]([CH2:16][CH2:15][CH2:14][O:13][CH:10]([CH3:12])[CH3:11])[C:25]=1[C:26]([O:28][CH3:29])=[O:27]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 671522-(Ethoxymethylene)propanedinitrileHCID 761943-Isopropoxypropylamine

Product 1

HCID 23033050HCID 23033050, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

After dissolving ethoxymethylenemalononitrile (10.2 g) in acetonitrile (200 mL), 3-isopropoxypropylamine (9.8 g) was added thereto and the mixture was stirred for 10 minutes. Cesium carbonate (68 g) and methyl bromoacetate (32 g) were added and the mixture was heated to reflux for 30 minutes. After cooling to room temperature, 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 saturated brine and then dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in ethyl acetate and passed through a silica gel, and then ethyl acetate (200 mL) was added for elution. The eluate was concentrated under reduced pressure to obtain a methyl 3-amino-4-cyano-1-[3-(methylethoxy)propyl]pyrrole-2-carboxylate crude product as a brown oil.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 30 minutes
  4. customthe supernatant was separated by decantation
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionwere added
  7. extractionextraction
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. dissolutionThe residue was dissolved in ethyl acetate
  12. additionethyl acetate (200 mL) was added for elution
  13. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a8e2f9e026ea4a568003f19f3426f8a0
Source dataset
uspto-grants-2009_05
Patent number
US07528140B2

Reaction notes

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