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

HRID 849763Notes

Reaction equation

HRID 849763 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+].[C:10]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1.CCCCCC>[C:2]([N:6]([C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:7][C:16]([C:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=1)=[O:17])([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 4

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide3×HCID 81889tert-Butylhydrazine monohydrochlorideHCID 1420661-Cyclohexenecarbonyl chloride

Product 1

HCID 15451994N'-t-butyl-N-cyclohexenylcarbonyl-N'-benzoylhydrazine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred suspension of t-butylhydrazine hydrochloride (0.86 g, 0.007M) in toluene (30 ml) was added 50% sodium hydroxide (0.55 g, 0.007M). After 15 minutes, the mixture was cooled to 5° C. and cyclohexenylcarbonyl chloride (1.0 g, 0.007M) and 50% sodium hydroxide (0.55 g, 0.007M) 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 hr. The mixture was diluted with hexane and the solid product isolated by filtration. This product (1.2 g, 0.006M) was dissolved in toluene (30 ml) and cooled on ice while stirring. To this mixture was added benzoylchloride (1.0 g, 0.007M) and 50% sodium hydroxide (1.3 g, 0.007M) simultaneously. After addition, the mixture was stirred for 1/2 hr., diluted with hexane and the solid product, N'-t-butyl-N-cyclohexenylcarbonyl-N'-benzoylhydrazine, isolated by filtration.

Workup

  1. temperaturesimultaneously so as to maintain the reaction temperature below 10° C
  2. additionAfter the addition
  3. temperatureto warm to room temperature
  4. customthe solid product isolated by filtration
  5. temperaturecooled on ice
  6. stirringwhile stirring
  7. additionAfter addition
  8. stirringthe mixture was stirred for 1/2 hr

Sources & evidence

ORD record
ord-6d5ca1b9f4054febacf23bda7f174b4b
Source dataset
uspto-grants-2000_01
Patent number
US06013836

Reaction notes

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