Phenylhydrazine → 1,5-Diphenyl-4,5-dihydro-1H-pyrazol-3-amine

HRID 2198975Notes

Reaction equation

HRID 2198975 reaction equation
[Na].[C:2]1([NH:8][NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10](#[N:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[NH2:19][C:10]1[CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 746673-Phenylprop-2-enenitrileHCID 5360545Sodium

Product 1

HCID 155806661,5-Diphenyl-4,5-dihydro-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.0 g. amount of sodium metal is dissolved in 150 ml. of absolute ethanol, then 40.0 ml. of phenylhydrazine is added followed in 5 minutes by 48.0 ml. of cinnamonitrile. The reaction mixture is refluxed for 3 hours with exothermic crystallization of a product. The product is collected by filtration and washed with water. The material is recrystallized from absolute ethanol to give 56.0 g. of the desired product as a solid, m.p. 195°-197° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours with exothermic crystallization of a product
  2. filtrationThe product is collected by filtration
  3. washwashed with water
  4. customThe material is recrystallized from absolute ethanol
  5. customto give 56.0 g

Sources & evidence

ORD record
ord-15ab82d078e34e3ca99e3fc2e8faa3b4
Source dataset
uspto-grants-1982_11
Patent number
US04360680

Reaction notes

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