2-Chloroacrylonitrile → 1-tert-Butyl-1H-pyrazol-5-amine

HRID 605596Notes

Reaction equation

HRID 605596 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[C:15]([NH2:16])=[CH:14][CH:17]=[N:7]1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

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

Product 1

HCID 398690981-tert-Butyl-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 600 ml of ethanol were successively added 59.94 g of tert-butylhydrazine hydrochloride, 79.3 g of sodium acetate and 50 ml of 2-chloroacrylonitrile at room temperature, followed by stirring the reaction mixture at 80° C. for 12 hours. After removing the solvent in vacuo, water was added to the residue. The mixture was neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The obtained ethyl acetate solution was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The obtained residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=2/1-1/2) to give the title compound as a pale yellow oil.

Workup

  1. customat room temperature
  2. customAfter removing the solvent in vacuo, water
  3. additionwas added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe obtained ethyl acetate solution was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe obtained residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate=2/1-1/2)

Sources & evidence

ORD record
ord-f8fbf19698334d699d5091498afb78e9
Source dataset
uspto-grants-2011_03
Patent number
US07915263B2

Reaction notes

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