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

HRID 579224Notes

Reaction equation

HRID 579224 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:21])[C:13]([N:15]([CH3:20])[N:16]=C(C)C)=[O:14])[CH3:2].Cl>O1CCCC1>[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:21])[C:13]([N:15]([CH3:20])[NH2:16])=[O:14])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866893431-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylethylidene)hydrazine

Product 1

HCID 569428781-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazineYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 500 ml volume four-necked flask, 1-[(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylethylidene)hydrazine (18-a) (21.41 g) and tetrahydrofuran (150 ml) were added under a nitrogen atmosphere at room temperature. To the mixture, 10% by weight of hydrochloric acid (29.23 g) was added dropwise over 5 minutes, and stirred at room temperature for 1 hour. Then, the reaction mixture was concentrated under reduced pressure. To the residue was added water (60 ml), and extracted with tert-butyl methyl ether. The organic layer was concentrated under reduced pressure, and added hexane (50 ml). The precipitated crystal was collected by filtration and dried to give 12.70 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methylhydrazine ((12-2)-(11)-39).

Workup

  1. concentrationThen, the reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added water (60 ml)
  3. extractionextracted with tert-butyl methyl ether
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. additionadded hexane (50 ml)
  6. filtrationThe precipitated crystal was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-2a2e69281b064c41802906cc46520a19
Source dataset
uspto-grants-2015_05
Patent number
US09040709B2

Reaction notes

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