Dimethylformamide → HCID 22024319, compound

HRID 500990Notes

Reaction equation

HRID 500990 reaction equation
[Cl-].[NH4+].[C-]#N.[K+].[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1/[CH:14]=[CH:15]/[C:16](=[O:18])[CH3:17].[CH3:19][N:20](C)C=O>O>[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[CH:14]([C:19]#[N:20])[CH2:15][C:16](=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 25517Ammonium ChlorideHCID 22024499HCID 22024499, compound

Product 1

HCID 22024319HCID 22024319, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ammonium chloride (6.84 g, 0.126 mol) and potassium cyanide (13.68 g, 0.210 mol) were added to a mixed solution (100 mL) of a 15% aqueous solution of (E)-4-(2,4-dimethylphenyl)-3-butene-2-one (18.32 g, 0.105 mol) and N,N-dimethylformamide, and the mixture was heated under reflux for 6 hours. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5) to give the title compound (10.13 g, 48%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with an aqueous saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:5)

Sources & evidence

ORD record
ord-6f49095d42454a4fb6355d0d4386f6ec
Source dataset
uspto-grants-2010_08
Patent number
US07772249B2

Reaction notes

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