Water → HCID 15617772, compound

HRID 1741860Notes

Reaction equation

HRID 1741860 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].O.[OH-].[Na+].[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15](Cl)=[O:16]>C1(C)C=CC=CC=1>[Cl:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][CH:20]=1)[C:15]([NH:7][NH:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 69252Benzoyl chloride, 3-chloro-HCID 81889tert-Butylhydrazine monohydrochloride

Product 1

HCID 15617772HCID 15617772, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of t-butyl hydrazine hydrochloride (6.2 g, 0.05 mole), water (30 mL) and toluene (60 mL) at 0° C. to 5° C. was added 50% sodium hydroxide (4.0 g,0.05 mol). To the above reaction mixture was then added, separately and simultaneously, 50% sodium hydroxide (4.0 g,0.05 mol) and 3-chlorobenzoyl chloride (8.8 g, 0.05 mol) from two dropping funnels. After addition was completed, the reaction mixture was stirred at 0° C. for 30 minutes and room temperature for 30 minutes. The resultant precipitate was collected by suction-filtration and washed with water (100 mL) and dried in air to give 9.0 g (79% yield) of 1-(3-chlorobenzoyl)-2-t-butyl hydrazine as a white solid. mp 116°-118° C.

Workup

  1. additionTo the above reaction mixture was then added
  2. additionAfter addition
  3. filtrationThe resultant precipitate was collected by suction-filtration
  4. washwashed with water (100 mL)
  5. customdried in air

Sources & evidence

ORD record
ord-36ab2f6c450a4015b6df607b9667db5f
Source dataset
uspto-grants-1994_08
Patent number
US05334726

Reaction notes

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