Potassium Iodide → HCID 10404499, compound

HRID 849300Notes

Reaction equation

HRID 849300 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1.[C:11]([NH:14][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:13])[CH3:12].[I-].[K+].[O-]CC.[Na+]>O1CCOCC1.C(O)C.[Cl-].[Na+].O.O>[CH2:24]([O:23][C:21](=[O:22])[C:15]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[N:10])[CH:4]=1)([NH:14][C:11](=[O:13])[CH3:12])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH3:25]

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 14041Acetamidomalonic acid diethyl esterHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 2723922Sodium ethoxide

Product 1

HCID 10404499HCID 10404499, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of alpha-bromo-meta-tolunitrile (45.0 g, 0.24 mole), diethyl acetamidomalonate (48.0 g, 0.22 mole) and potassium iodide ((3.0 g, 0.018 mole) in dioxane (500 mL) was added 2.5M sodium ethoxide in ethanol (100 mL) dropwise under an argon atmosphere. After the addition was complete, the solution was refluxed for 6 hours. The reaction mixture was allowed to stand overnight at room temperature, then diluted with brine (250 mL) and water (250 mL), and extracted with ethyl acetate four times (1.0 L total). The combined extracts were washed with water (100 mL), 10% citric acid (100 mL), water (100 mL) and brine (2×50 mL), then dried over anhydrous magnesium sulfate and filtered; the solvent was removed under vacuum. The crude residue was recrystallized from ethyl acetate and diethyl ether in two crops to yield 43.51 g (60%) of the 3-cyanobenzyl-N-acetylaminomalonic acid diethyl ester as yellow crystals.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was refluxed for 6 hours
  3. extractionextracted with ethyl acetate four times (1.0 L total)
  4. washThe combined extracts were washed with water (100 mL), 10% citric acid (100 mL), water (100 mL) and brine (2×50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed under vacuum
  8. customThe crude residue was recrystallized from ethyl acetate and diethyl ether in two crops

Sources & evidence

ORD record
ord-09896df783834f74b9ce7c44ffc5f7c3
Source dataset
uspto-grants-2000_01
Patent number
US06011158

Reaction notes

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