Benzoyl chloride → N'-tert-butylbenzohydrazide

HRID 1461564Notes

Reaction equation

HRID 1461564 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 (1.24 g, 10 mmol) in toluene (30 ml) at room temperature was added dropwise a 50% aqueous solution of sodium hydroxide (0.8 g, 10 mmole). After 15 min., the reaction mixture was cooled to 5° C. and a solution of benzoyl chloride (1.42 g, 10 mmol) in toluene (5 ml) and a solution of 50% aqueous sodium hydroxide (0.8 g, 10 mmol) were added dropwise simultaneously from separate addition funnels while maintaining the temperature at or below 10°. Following the addition, the reaction mixture was warmed to room temperature and stirred for 1 hr. The reaction mixture was diluted with toluene washed with water. The organic layer was separated, dried over anhydrous magnesium sulfate, and the solvent removed under vacuum to afford a yellow oil which slowly solidified on standing. The product was recrystallized from ethyl ether:hexane to afford white crystals.

Workup

  1. customfrom separate
  2. additionaddition funnels
  3. temperaturewhile maintaining the temperature at or below 10°
  4. additionthe addition
  5. temperaturethe reaction mixture was warmed to room temperature
  6. additionThe reaction mixture was diluted with toluene
  7. washwashed with water
  8. customThe organic layer was separated
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent removed under vacuum
  11. customto afford a yellow oil which
  12. customThe product was recrystallized from ethyl ether
  13. customhexane to afford white crystals

Sources & evidence

ORD record
ord-23ae32a58d4a43daac90df81de96f28d
Source dataset
uspto-grants-1991_12
Patent number
US05075471

Reaction notes

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