Benzoyl chloride → N'-t-butyl-N-phenylacetyl-N'-benzoylhydrazine

HRID 21634Notes

Reaction equation

Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[C:10]1([CH2:16][C:17](Cl)=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C=CC=CC=1.CCCCCC>[C:2]([N:6]([C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:7][C:17](=[O:18])[CH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 5 °C

Procedure

To a stirred suspension of t-butylhydrazine hydrochloride (2.0 g, 0.016M) in toluene (30 ml) was added 50% sodium hydroxide (1.3 g, 0.016M). After 15 minutes, the mixture was cooled to 5° C. and phenylacetyl chloride (2.4 g, 0.016M) and 50% sodium hydroxide (1.3 g, 0.016M) were added separately and simultaneously so as to maintain the reaction temperature below 10° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The mixture was diluted with hexane and the solid product isolated by filtration. This product (3.2 g, 0.015M) was dissolved in a stirred mixture of toluene (30 ml) and cooled on ice. To this mixture was added benzoylchloride (2.2 g, 0.016M) and 50% sodium hydroxide (1.3 g, 0.016M) simultaneously. After addition, the mixture was stirred for 1/2 hour, diluted with hexane and the solid product, N'-t-butyl-N-phenylacetyl-N'-benzoylhydrazine, isolated by filtration.

Workup

temperaturesimultaneously so as to maintain the reaction temperature below 10° C
additionAfter the addition
temperatureto warm to room temperature
customthe solid product isolated by filtration
temperaturecooled on ice
additionAfter addition
stirringthe mixture was stirred for 1/2 hour

Sources & evidence

ORD record: ord-5d4415c8f6eb4a69a72e4f28887b0d14
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05424333

Reaction notes

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