Sodium Hydroxide → HCID 86737146, compound

HRID 1856123Notes

Reaction equation

HRID 1856123 reaction equation
Cl.[C:2]([NH:7][NH2:8])([CH2:5][CH3:6])([CH3:4])[CH3:3].[C:9]([O:16][CH2:17][CH:18]=[CH2:19])(=[O:15])[CH2:10][CH2:11][C:12]([CH3:14])=O.[OH-].[Na+]>O>[C:2]([NH:7][N:8]=[C:12]([CH3:14])[CH2:11][CH2:10][C:9]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])([CH2:5][CH3:6])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 117545Hydrazine, (1,1-dimethylpropyl)-, monohydrochlorideHCID 529770Allyl 4-oxopentanoate

Product 1

HCID 86737146HCID 86737146, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 1 liter round bottom flask equipped with a magnetic stirrer and water-cooled condenser was added 760 grams (0.5 mole) of a 9.1% aqueous solution of t-amylhydrazine hydrochloride, 78 grams (0.5 mole) of allyl levulinate and 40 grams (0.5 mole) of 50% sodium hydroxide. The flask was placed in an oil bath on a magnetic stirrer and the contents stirred and heated to reflux. The reaction was refluxed gently for 3 hours and allowed to cool to room temperature. The organic layer was separated, dried over anhydrous sodium sulfate and the drying agent removed by filtration. The yellow liquid product weighed 116 grams (96.5% crude yield). The infrared spectrum of the product contained a strong band at 1718 cm-1 (carbonyl) and a weak band at 1620 cm-1 (C=N) indicating that the hydrazone band had formed and the ester group was still intact.

Workup

  1. customTo a 1 liter round bottom flask equipped with a magnetic stirrer
  2. customThe flask was placed in an oil bath on a magnetic stirrer
  3. temperatureheated to reflux
  4. temperatureThe reaction was refluxed gently for 3 hours
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe drying agent removed by filtration
  8. customhad formed

Sources & evidence

ORD record
ord-0969b309a5064ee187ee7d70573bdfe9
Source dataset
uspto-grants-1980_08
Patent number
US04218370

Reaction notes

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