Potassium Iodide → Diethyl 4-cyanobenzylacetamidomalonate

HRID 963947Notes

Reaction equation

HRID 963947 reaction equation
C([CH:3]([CH2:14][CH3:15])[C:4]([NH:6][CH:7]([C:11]([O-:13])=[O:12])[C:8]([O-:10])=[O:9])=[O:5])C.BrCC1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1.[I-].[K+].[O-][CH2:29][CH3:30].[Na+].O1CCO[CH2:34][CH2:33]1>>[C:24]([C:21]1[CH:20]=[CH:19][C:15]([CH2:14][CH2:3][C:4]([NH:6][CH:7]([C:11]([O:13][CH2:29][CH3:30])=[O:12])[C:8]([O:10][CH2:33][CH3:34])=[O:9])=[O:5])=[CH:23][CH:22]=1)#[N:25]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 312751,4-DioxaneHCID 869964-(Bromomethyl)benzonitrileHCID 2723922Sodium ethoxideHCID 21751412Diethylacetamidomalonate

Product 1

HCID 33254412Diethyl 4-cyanobenzylacetamidomalonateYield 91%

Procedure

Suspend diethylacetamidomalonate (44 g, 0.203 mol), alpha-bromo-p-toluonitrile (40 g, 0.204 mol), potassium iodide (10 g) in dioxane (400 mL) and add a solution of sodium ethoxide (4.6 g of sodium in 200 mL of dry ethanol). Heat under reflux the mixture for 3-4 hours and let stay overnight. Pour the mixture on ice (2 L), filtrate the precipitate, wash with water and dry on lyophyliser. Recrystallize from methanol, to give diethyl 4-cyanobenzylacetamidomalonate as white crystals (61 g, 91%).

Workup

  1. temperatureHeat
  2. temperatureunder reflux the mixture for 3-4 hours
  3. additionPour the mixture on ice (2 L), filtrate the precipitate
  4. washwash with water
  5. customdry on lyophyliser
  6. customRecrystallize from methanol

Sources & evidence

ORD record
ord-337318d7450b453fad4e23045aaf1595
Source dataset
uspto-grants-1998_06
Patent number
US05766932

Reaction notes

Loading…