Sodium Hydroxide → N'-Benzoyl-3,4-dichloro-N-(2-methyl-2-propanyl)benzohydrazide

HRID 1463561Notes

Reaction equation

HRID 1463561 reaction equation
[C:1]([NH:9][NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:17][C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][C:26]=1[Cl:27])[C:21](Cl)=[O:22]>C(Cl)Cl>[C:1]([NH:9][N:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:21](=[O:22])[C:20]1[CH:24]=[CH:25][C:26]([Cl:27])=[C:18]([Cl:17])[CH:19]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 76403Benzoyl chloride, 3,4-dichloro-HCID 299436N'-tert-butylbenzohydrazide

Product 1

HCID 15617782N'-Benzoyl-3,4-dichloro-N-(2-methyl-2-propanyl)benzohydrazideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Benzoyl-2-tert-butylhydrazine (4.8 g, 0.025 mole) is stirred vigorously in a two-phase system of 50 mL of methylene chloride and 25 mL of 10% aqueous sodium hydroxide (2.5 g, 0.063 mole) until all dissolves. To this solution is added a solution of 3,4-dichlorobenzoyl chloride (7.3 g, 0.025 mole) in methylene chloride. After stirring the two-phase mixture several hours at ambient temperature, the solid is removed and washed with water and methylene chloride. Recrystallization from 2-propanol gives 7.1 g (78%) of product with mp 234°-235.5° C.

Workup

  1. customthe solid is removed
  2. washwashed with water and methylene chloride
  3. customRecrystallization from 2-propanol

Sources & evidence

ORD record
ord-c95f4532655b4590b6f8d41ea60ae4c8
Source dataset
uspto-grants-1994_04
Patent number
US05300688

Reaction notes

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