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Pivaloyl chloride → 2'-(2-Chloro-4-nitrophenyl)-2,2-dimethylpropionohydrazide

HRID 46723
Notes
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Reaction equation

HRID 46723 reaction equation
[Cl: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>[Cl: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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 5029294(2-Chloro-4-nitrophenyl)hydrazine

Product 1

HCID 441539972'-(2-Chloro-4-nitrophenyl)-2,2-dimethylpropionohydrazideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred and chilled (0° C.) solution containing 25 g (0.133 mol) of 2-chloro-4-nitrophenylhydrazine and 18.06 g (0.14 mol) of ethyldiisopropylamine in 200 ml of tetrahydrofuran was added dropwise 16.75 g (0.139 mol) of pivaloyl chloride. The reaction mixture was briefly heated to reflux and then concentrated under reduced pressure. The residue was treated with water, filtered and dried to give 32.5 g (90% yield) of the desired product as a yellowish solid; m.p. 123° C.

Workup

  1. temperatureThe reaction mixture was briefly heated
  2. temperatureto reflux
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was treated with water
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-71be4ad80a0e49a4b465031a96b40252
Source dataset
uspto-grants-1979_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04174958

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes