Water → 1-(2-Chloro-5-nitrophenyl)-2-(2,2-dimethylpropionyl)hydrazine

HRID 1165928Notes

Reaction equation

HRID 1165928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][NH2:12].C(N(CC)CC)C.[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][NH:12][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 4103137(2-Chloro-5-nitrophenyl)hydrazine

Product 1

HCID 142806541-(2-Chloro-5-nitrophenyl)-2-(2,2-dimethylpropionyl)hydrazineYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-5-nitrophenylhydrazine (37.60 g) in dichloromethane (200 ml), triethylamine (22.27 g) and pivaloyl chloride (26.59 g) were added, and the resultant mixture was stirred at room temperature for 12 hours. The reaction mixture was combined with water. The dichloromethane layer was washed with water, dried and concentrated under reduced pressure to give 1-(2-chloro-5-nitrophenyl)-2-(2,2-dimethylpropionyl)hydrazine (42.23 g). m.p., 153.3° C..

Workup

  1. washThe dichloromethane layer was washed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b0224c2604e45d4a79598f762f80c84
Source dataset
uspto-grants-1990_03
Patent number
US04912225

Reaction notes

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