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

HRID 335469

Reaction equation

HRID 335469 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].[CH2:25](C(C)=O)C(C)C.[C:32](=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][CH3:32])[CH3:2]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 7909Methyl Isobutyl KetoneHCID 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 100 mL volume three-necked flask, 5.0 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(phenylmethylidene)hydrazine ((40-a)-(14)-6), 31 ml of methyl isobutyl ketone, 6.43 g of potassium carbonate and 1.75 ml of dimethyl sulfate were added and the mixture was stirred at room temperature for 7.5 hours. Water was added to the reaction mixture, the organic layer was removed and then the aqueous layer was extracted with 31 ml of methyl isobutyl ketone. The organic layers were combined, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.324 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine ((40-b)-(15)-5)) and 0.324 g of methyl 2-(2,6-diethyl-4-methylphenyl)-2-oxo-N-(phenylmethylidene)ethanehydrazonate (X-1).

Workup

  1. customthe organic layer was removed
  2. extractionthe aqueous layer was extracted with 31 ml of methyl isobutyl ketone
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85d1becec7044685bfa425d5da985022
Source dataset
uspto-grants-2014_11
Patent number
US08884010B2

Linked notes

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