2-Chloroacrylonitrile → 1-tert-Butyl-1H-pyrazol-3-amine

HRID 421990Notes

Reaction equation

HRID 421990 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].C([O-])(=O)C.[Na+].Cl[C:14](=[CH2:17])[C:15]#[N:16]>C(O)C>[C:2]([N:6]1[CH:17]=[CH:14][C:15]([NH2:16])=[N:7]1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 701982-ChloroacrylonitrileHCID 81889tert-Butylhydrazine monohydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 132175721-tert-Butyl-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 600 ml of ethanol were added 59.94 g of tert-butylhydrazine hydrochloride, 79.3 g of sodium acetate and 2-chloroacrylonitrile followed by stirring at 80° C. for 12 hours. After removal of the solvent, water was added and then was neutralized with sodium hydrogen carbonate followed by extracting with ethyl acetate. The resulting organic layer was washed with saturated brine, and then dried over magnesium sulfate. The organic layer was filtered and concentrated in vacuo. The resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/2) to give the title compound.

Workup

  1. customAfter removal of the solvent, water
  2. additionwas added
  3. extractionby extracting with ethyl acetate
  4. washThe resulting organic layer was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/2)

Sources & evidence

ORD record
ord-ea54a4dac266461e9aef40dd0300e0a7
Source dataset
uspto-grants-2012_01
Patent number
US08101621B2

Reaction notes

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