Hydrochloric Acid → 1-[2-(2,4,6-Triethylphenyl)-2-oxoacetyl]-1-methylhydrazine

HRID 579266Notes

Reaction equation

HRID 579266 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[C:4]=1[C:13](=[O:22])[C:14]([N:16]([CH3:21])[N:17]=C(C)C)=[O:15])[CH3:2].C(O)C.Cl.CCCCCC>C(OCC)(=O)C>[CH2:1]([C:3]1[CH:8]=[C:7]([CH2:9][CH3:10])[CH:6]=[C:5]([CH2:11][CH3:12])[C:4]=1[C:13](=[O:22])[C:14]([N:16]([CH3:21])[NH2:17])=[O:15])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8058HexaneHCID 866893591-[2-(2,4,6-Triethylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylethylidene)hydrazine

Product 1

HCID 666955611-[2-(2,4,6-Triethylphenyl)-2-oxoacetyl]-1-methylhydrazineYield 16.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 100 ml volume four-necked flask, 1-[2-(2,4,6-triethylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylethylidene)hydrazine (18-b) (21.41 g) and ethanol (35 ml) were added under a nitrogen atmosphere, 10 w/w % of hydrochloric acid (14.54 g) was added and stirred at room temperature for 2.5 hours. The reaction mixture was concentrated under reduced pressure. To the residue, saturated brine was added and extracted with chloroform (120 ml×1, 60 ml×2). The organic layers were combined, and dried over anhydrous magnesium sulfate. After the inorganic salt was removed by filtration, the filtrate was concentrated under reduced pressure to give 19.08 g of a crude product. The crude product was subjected to column chromatography (hexane: ethyl acetate=2:1 to 1:1) to give 3.008 g of 1-[2-(2,4,6-triethylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-40).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue, saturated brine was added
  3. extractionextracted with chloroform (120 ml×1, 60 ml×2)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the inorganic salt was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto give 19.08 g of a crude product

Sources & evidence

ORD record
ord-8eac848925594b60924a67af1087ecc0
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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