Pivaloyl chloride → Pivalic acid 2-(2-bromo-4-nitrophenyl)hydrazide

HRID 46722Notes

Reaction equation

HRID 46722 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][NH2:12].C(N(C(C)C)C(C)C)C.[C:22](Cl)(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][NH:12][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 37800652-Bromo-4-nitro-phenyl-hydrazine

Product 1

HCID 53671610Pivalic acid 2-(2-bromo-4-nitrophenyl)hydrazideYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred and chilled (0°) solution containing 200 g (0.86 mol) of 2-bromo-4-nitrophenylhydrazine (m.p. 143°-145°) and 116.8 g (0.9 mol) of ethyldiisopropylamine in 1000 ml of tetrahydrofuran was added dropwise 108.5 g (0.9 mol) of pivaloyl chloride. The reaction mixture was stirred at ambient temperature for 1 hour and then concentrated to dryness under reduced pressure. The residue was treated with water, filtered and recrystallized from ethanol to give 165 g (52%) of product as a light yellow solid; m.p. 145° C.

Workup

  1. temperaturechilled (0°) solution
  2. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  3. concentrationconcentrated to dryness under reduced pressure
  4. additionThe residue was treated with water
  5. filtrationfiltered
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-190279ac6ac94ac49644cabe172141dd
Source dataset
uspto-grants-1979_11
Patent number
US04174958

Reaction notes

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