Hydrazine hydrate (1:1) → HCID 55285667, compound

HRID 1943931Notes

Reaction equation

HRID 1943931 reaction equation
[CH:1]([NH:4]/[C:5](/SC)=[CH:6]/[C:7]#[N:8])([CH3:3])[CH3:2].O.[NH2:12][NH2:13]>CCO>[CH:1]([NH:4][C:5]1[CH:6]=[C:7]([NH2:8])[NH:13][N:12]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86652503(2Z)-3-[(1-Methylethyl)amino]-3-(methylthio)-2-propenenitrile

Product 1

HCID 55285667HCID 55285667, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (Z)-3-(isopropylamino)-3-(methylthio)acrylonitrile (0.413 g, 2.64 mmol) and hydrazine monohydrate (0.38 mL, 7.93 mmol) in EtOH (6 mL) was heated to reflux for 16 hours. After cooling to room temperature, the reaction mixture was concentrated. The residue was purified by column chromatography, eluting with ethyl acetate, DCM/MeOH (9:1) to give N3-isopropyl-1H-pyrazole-3,5-diamine (0.231 g, 62% over 2 steps) as an oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. concentrationthe reaction mixture was concentrated
  4. customThe residue was purified by column chromatography
  5. washeluting with ethyl acetate, DCM/MeOH (9:1)

Sources & evidence

ORD record
ord-1aa0d19f5a26406592838b4bfdc8bdfc
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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