Bromide ion → N-benzyl-N'-t-butyl-N,N'-dibenzoylhydrazine

HRID 483455Notes

Reaction equation

HRID 483455 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+].[Br-].Cl>CN(C=O)C.O>[CH2:7]([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)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 259Bromide ionHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 863071,2-Dibenzoyl-1-(tert-butyl)hydrazine

Product 1

HCID 1275953N-benzyl-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 (2 g, 0.006M) in DMF (25 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.3 g, 0.007M). The mixture was stirred at room temperature for 0.5 hours, and thenbenzyl bromide (1.2 g, 0.007M) was added dropwise. The reaction mixture was warmed to 60° C. and allowed to stir for 2 hours. The mixture was then diluted with water (50 ml), neutralized with 1% 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-benzyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

Workup

  1. temperatureThe reaction mixture was warmed to 60° C.
  2. stirringto stir 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-9aef503aac5044ecab4a0402a5b27435
Source dataset
uspto-grants-1993_07
Patent number
US05225443

Reaction notes

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