Acetone → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine

HRID 579282Notes

Reaction equation

HRID 579282 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:24])[C:13]([NH:15][N:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])[CH3:2].[CH3:25]C(C)=O.[C:29](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>O>[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:24])[C:13]([N:15]([CH3:25])[N:16]=[CH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:14])[CH3:2].[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:24])[C:13](=[N:15][N:16]=[CH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[O:14][CH3:29])[CH3:2]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 666919781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-2-(phenylmethylidene)hydrazine

Product 2

HCID 666915621-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazineHCID 86689363methyl 2-(2,6-diethyl-4-methylphenyl)-2-oxo-N-(phenylmethylidene)ethanehydrazonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL volume three-necked flask, 300 mg of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(phenylmethylidene)hydrazine ((40-a)-(14)-6), 1.9 ml of acetone, 386 mg of potassium carbonate and 152 mg of dimethyl sulfate were added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture and the resultant was extracted with ethyl acetate three times. The organic layers were combined and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=10:1) to give 261 mg of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine ((40-b)-(15)-5) and 28 mg of methyl 2-(2,6-diethyl-4-methylphenyl)-2-oxo-N-(phenylmethylidene)ethanehydrazonate (compound (x-1)).

Workup

  1. extractionthe resultant was extracted with ethyl acetate three times
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d6a70a06ab64eb5ad7f682d4a0dd0d8
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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