Benzoyl chloride → 1,2-Dibenzoyl-1-(tert-butyl)hydrazine
Reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-:8].[Na+].[C:10](Cl)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1(C)C=CC=CC=1>[C:2]([N:6]([C:10](=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:7][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([CH3:5])([CH3:4])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a stirred suspension of t-butylhydrazine hydrochloride (1.24 g, 10 mmoles) in toluene (50 ml) at room temperature, was added dropwise a solution of 50% aqueous sodium hydroxide (0.8 g, 10 ml). After 15 minutes, the reaction mixture was cooled to 5° C. and solutions of benzoyl chloride (2.82 gm, 20 ml) in toluene (7 ml) and 50% aqueous sodium hydroxide (1.6 g) were added dropwise and simultaneously from separate addition funnels while maintaining the temperature below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with ether and the product isolated by filtration. The product was washed with water and ether and dried. The product was recrystallized from ethermethanol to afford N'-t-butyl-N,N'-dibenzoylhydrazine as a white powder: m.p. 174-176° C.
Workup
- customsimultaneously from separate
- additionaddition funnels
- temperaturewhile maintaining the temperature below 10° C
- additionthe addition
- temperaturethe reaction mixture was warmed to room temperature
- additionThe reaction mixture was diluted with ether
- customthe product isolated by filtration
- washThe product was washed with water and ether
- customdried
- customThe product was recrystallized from ethermethanol
Sources & evidence
- ORD record
- ord-1d55d96adc55411db1bf041bf3e2639e
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06013836
Reaction notes
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