Benzoyl chloride → 1,2-Dibenzoyl-1-(tert-butyl)hydrazine

HRID 849751Notes

Reaction equation

HRID 849751 reaction equation
[C:1]([OH:6])(=O)[C:2](O)=O.[CH3:7][C:8]([NH:11][NH2:12])([CH3:10])[CH3:9].[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.[OH-].[Na+].CCCCCC>[CH3:7][C:8]([N:11]([C:1](=[O:6])[C:2]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1)[NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 269219Tert-butylhydrazine ethanedioate(1:1)

Product 1

HCID 863071,2-Dibenzoyl-1-(tert-butyl)hydrazineYield 15%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

The 1,1-dimethylethylhydrazine oxalate (2 g) was dissolved in toluene and neutralized with 50% aqueous sodium hydroxide. To this solution was added benzoyl chloride (4.02 g) and sodium hydroxide (50% Aq. solution) (2.45 g) at 25° C. The reaction mixture was warmed to room temperature and stirred 3 hours. The mixture was diluted with hexane and filtered to afford the product as a white solid (0.5 g).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-153c606ec5164b559ef96c6a03f6367b
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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