2-Acetylbutyrolactone → 3-((E)-1-[3-Methyl-1-(2,4,6-trichlorophenyl)-1H-5-pyrazolyl]aminoethylidene)tetrahydro-2-furanone

HRID 890184

Reaction equation

HRID 890184 reaction equation
[NH2:1][C:2]1[N:3]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[N:4]=[C:5]([CH3:7])[CH:6]=1.[C:17]([CH:20]1[CH2:25][CH2:24][O:23][C:21]1=[O:22])(=O)[CH3:18]>C(O)C>[CH3:7][C:5]1[CH:6]=[C:2]([NH:1]/[C:17](=[C:20]2/[C:21](=[O:22])[O:23][CH2:24][CH2:25]/2)/[CH3:18])[N:3]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:9]=2[Cl:16])[N:4]=1

Participants

4

Reactant 2

HCID 106012-AcetylbutyrolactoneHCID 20600323-Methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazol-5-amine

Product 1

HCID 222495073-((E)-1-[3-Methyl-1-(2,4,6-trichlorophenyl)-1H-5-pyrazolyl]aminoethylidene)tetrahydro-2-furanoneYield 49.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-2-(2,4,6-trichlorophenyl)-5-methylpyrazole (1 g, 3.62 mmol) was dissolved in ethanol (10 mL). α-Acetyl-γ-butyrolactone (0.409 mL, 3.80 mmol) was added, followed by heating under reflux for two days. After ethanol was evaporated, the residue was purified by silica gel column chromatography (10% ethyl acetate/hexane), to give the title compound (700 mg, 1.80 mmol) as a pale yellow oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for two days
  3. customAfter ethanol was evaporated
  4. customthe residue was purified by silica gel column chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-4a991ae114bf42a28a6945ad5afb4faa
Source dataset
uspto-grants-2006_02
Patent number
US06995163B2

Linked notes

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