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

HRID 621369Notes

Reaction equation

HRID 621369 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-bfb826ccda3941b08c92bfee3f6fa0b7
Source dataset
uspto-grants-1989_04
Patent number
US04824465

Reaction notes

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