Phenylacetyl chloride → N'-t-butyl-N-benzoyl-N'-phenylacetylhydrazine

HRID 849796Notes

Reaction equation

HRID 849796 reaction equation
[C:1]([NH:5][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].[OH-].[Na+].[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C=CC=CC=1.CCCCCC>[C:1]([N:5]([C:24](=[O:25])[CH2:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 14798Sodium HydroxideHCID 299436N'-tert-butylbenzohydrazide

Product 1

HCID 15451997N'-t-butyl-N-benzoyl-N'-phenylacetylhydrazineYield 90%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

N'-t-butyl-N-benzoylhydrazine (2 g) was stirred in toluene (35 ml) and 50% aqueous sodium hydroxide (1 g) at 5° C. Phenylacetylchloride (1.5 g) was added slowly, dropwise to the reaction mixture, warmed to room temperature and stirred 1 hour. The reaction mixture was diluted with hexane (50 ml) and filtered off to yield a solid product. The filter cake was washed with hexane and water and allowed to air dry. The white solid product obtained in 90% yield melted at 167-169° C.

Workup

  1. customat 5° C
  2. filtrationfiltered off
  3. customto yield a solid product
  4. washThe filter cake was washed with hexane and water
  5. customto air dry
  6. customThe white solid product obtained in 90% yield melted at 167-169° C.

Sources & evidence

ORD record
ord-b2e053bcf9aa4099b5337f99b8275cba
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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