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

HRID 21619

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

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 ether-methanol 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 ether-methanol

Sources & evidence

ORD record: ord-e5a0fe37f56f4e1db3f99f85ac7ae677
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424333

Linked notes

Loading…