Benzoyl chloride → N'-tert-butylbenzohydrazide

HRID 21640

Reaction equation

HRID 21640 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].[OH-].[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]([NH:6][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

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2×HCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 299436N'-tert-butylbenzohydrazide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a stirred suspension of t-butylhydrazine hydrochloride (2 g, 0.016M) in toluene (50 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (1.28 g, 0.016M). After 15 minutes, the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (2.3 g, 0.017M) in toluene (5 ml) and a solution of aqueous 50% sodium hydroxide (1.36 g, 0.017M) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10° C. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hour. The reaction mixture was diluted with hexane and the solid N'-t-butyl-N-benzoylhydrazine was isolated by filtration.

Workup

  1. customfrom separate
  2. additionaddition funnels
  3. temperaturewhile maintaining the temperature at or below 10° C
  4. additionthe addition
  5. temperaturethe reaction mixture was warmed to room temperature
  6. additionThe reaction mixture was diluted with hexane

Sources & evidence

ORD record
ord-844de72b613a415f811a9289f1c17680
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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