Acetic Acid → HCID 178469261, compound

HRID 890176Notes

Reaction equation

HRID 890176 reaction equation
C(O)(=O)C.[C:5]1([CH3:20])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[C:13]1[C:14]([CH3:19])=[N:15][NH:16][C:17]=1[NH2:18].[C:21]([CH:24]([C:30](OCC)=[O:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])(=O)[CH3:22]>C1(C)C(C)=CC=CC=1>[C:5]1([CH3:20])[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:6]=1[C:13]1[C:14]([CH3:19])=[N:15][N:16]2[C:30](=[O:31])[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:21]([CH3:22])[NH:18][C:17]=12

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1363651,3-Diethyl 2-acetylpropanedioateHCID 178424562HCID 178424562, compound

Product 1

HCID 178469261HCID 178469261, compoundYield 36.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Acetic acid (5 mL) was added to a solution of 4-mesityl-3-methyl-1H-5-pyrazoleamine (5 g, 23.22 mmol) and diethyl 2-acetylmalonate (4.7 g, 23.22 mmol) in xylene (40 mL), followed by heating under reflux for seven hours. The reaction mixture was evaporated as it was, and water was added thereto. After extracting with ethyl acetate, the organic layer was washed with an aqueous saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane), to give the title compound (3 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for seven hours
  3. customThe reaction mixture was evaporated as it
  4. additionwater was added
  5. extractionAfter extracting with ethyl acetate
  6. washthe organic layer was washed with an aqueous saturated sodium bicarbonate and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated
  9. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-573e75969e434fada7dbb3234aa4c731
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Reaction notes

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