Acetophenone → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-phenyl-1-ethylidene)hydrazine

HRID 335466Notes

Reaction equation

HRID 335466 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:18])[C:13]([N:15]([CH3:17])[NH2:16])=[O:14])[CH3:2].O1CCCC1.[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=O)[CH3:25]>C(O)(=O)C>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12](=[O:18])[C:13]([N:15]([CH3:17])[N:16]=[C:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:25])=[O:14])[CH3:2]

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 8028TetrahydrofuranHCID 569428781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine

Product 1

HCID 866893621-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-phenyl-1-ethylidene)hydrazineYield 45.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 20 mL volume two-necked flask, 0.50 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-39), 10 ml of tetrahydrofuran (anhydrous), 0.27 g of acetophenone and 130 mg of acetic acid were added under a nitrogen atmosphere, and the mixture was stirred for 6 hours under reflux. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Water (60 ml) was added to the residue and the resultant was extracted with t-butyl methyl ether. The organic layer was concentrated under reduced pressure and subjected to silica gel column, chromatography (ethyl acetate:chloroform=3:1) to give 0.32 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-phenyl-1-ethylidene)hydrazine ((40-b)-(15)-6).

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated under reduced pressure
  3. additionWater (60 ml) was added to the residue
  4. extractionthe resultant was extracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-37885e275a644690a6875957a4155381
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Reaction notes

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