Hydrochloric Acid → N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine

HRID 849757Notes

Reaction equation

HRID 849757 reaction equation
[C:1]([N:5]([C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:25](I)[CH:26]=[CH2:27].Cl>CN(C=O)C.O>[CH2:27]([N:6]([C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:15](=[O:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH:26]=[CH2:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 863071,2-Dibenzoyl-1-(tert-butyl)hydrazine

Product 1

HCID 15294608N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N'-t-butyl-N,N'-dibenzoylhydrazine (3 g, 0.011 M) in DMF (30 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.5 g, 0.012 M). The mixture was stirred at room temperature for 0.5 hours, and then allyl iodide (1.8 g, 0.01 M) was added dropwise. The reaction mixture was warmed to 60° C. and stirred for 2 hours. The mixture was then diluted with water (50 ml), neutralized with 10% HCl, and the product extracted into methylene chloride (50 ml). The methylene chloride layer was washed with water (5×20 ml), dried over anhydrous magnesium sulfate, and the methylene chloride removed under vacuum to afford N-allyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

Workup

  1. temperatureThe reaction mixture was warmed to 60° C.
  2. stirringstirred for 2 hours
  3. extractionthe product extracted into methylene chloride (50 ml)
  4. washThe methylene chloride layer was washed with water (5×20 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe methylene chloride removed under vacuum

Sources & evidence

ORD record
ord-bd2c53c44e8d4fc282390948a46cf235
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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