Potassium Carbonate → Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate

HRID 1890226Notes

Reaction equation

HRID 1890226 reaction equation
[CH3:1][NH:2][N:3]=[C:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29](Cl)=[O:30])[CH3:18]>C(#N)C>[CH2:17]([C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[C:21]([CH2:26][CH3:27])[C:20]=1[CH2:28][C:29]([N:2]([CH3:1])[N:3]=[C:4]([CH3:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:30])[CH3:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 574373202,6-Diethyl-4-methylphenylacetyl chlorideHCID 73828661Ethyl 2-(methylhydrazono)propanoate

Product 1

HCID 76550641Ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoateYield 49.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of 2.0 g of ethyl 2-(methylhydrazono)propanoate and 35 mL of acetonitrile, 1.5 g of potassium carbonate was added. To the mixture, a solution of 2.6 g of 2,6-diethyl-4-methylphenylacetyl chloride in 10 mL of acetonitrile was added dropwise over about 20 minutes under ice cooling. This mixture was stirred at room temperature for 3.5 hours. The reaction mixture was concentrated under reduced pressure. To the residue, 20 mL of ice water was added, followed by extraction with ethyl acetate (20 mL×3). The organic layer was washed with an aqueous saturated sodium chloride solution (20 mL×2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to basic alumina column chromatography (ethyl acetate:hexane=1:3) to obtain 1.9 g of ethyl 2-[2-(2,6-diethyl-4-methylphenylacetyl)-2-methylhydrazono]propanoate [compound (VI-2)] as a white crystal.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the residue, 20 mL of ice water was added
  4. extractionfollowed by extraction with ethyl acetate (20 mL×3)
  5. washThe organic layer was washed with an aqueous saturated sodium chloride solution (20 mL×2)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64562c397b374f5dbf765357f39b36b2
Source dataset
uspto-grants-2013_08
Patent number
US08507410B2

Reaction notes

Loading…