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

HRID 21627

Reaction equation

HRID 21627 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+].[CH3:25]I.Cl>CN(C)C=O.O>[CH3:25][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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 863071,2-Dibenzoyl-1-(tert-butyl)hydrazine

Product 1

HCID 15294607N-methyl-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 (2.5 g, 0.008M) in dimethylformamide (DMF) (30 ml) at room temperature under nitrogen was added portionwise sodium hydride (60% oil dispersion) (0.4 g, 0.009M). The mixture was stirred at room temperature for 0.5 hours, and then methyl iodide (1.0 g, 0.008M) was added dropwise. The reaction mixture was allowed to stir for 1 hour. 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-methyl-N'-t-butyl-N,N'-dibenzoylhydrazine as an oil.

Workup

  1. stirringto stir for 1 hour
  2. extractionthe product extracted into methylene chloride (50 ml)
  3. washThe methylene chloride layer was washed with water (5×20 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe methylene chloride removed under vacuum

Sources & evidence

ORD record
ord-35fc4fbb2cec488f98f20d76710491b4
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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