Acrylonitrile → 1-(3,4-Dichlorophenyl)-4,5-dihydro-1H-pyrazol-3-amine

HRID 544633Notes

Reaction equation

HRID 544633 reaction equation
[Na].Cl.[Cl:3][C:4]1[CH:5]=[C:6]([NH:11][NH2:12])[CH:7]=[CH:8][C:9]=1[Cl:10].[C:13](#[N:16])[CH:14]=[CH2:15]>C(O)C>[NH2:16][C:13]1[CH2:14][CH2:15][N:11]([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=2)[N:12]=1

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 3084323(3,4-Dichlorophenyl)hydrazine monohydrochlorideHCID 5360545Sodium

Product 1

HCID 155806881-(3,4-Dichlorophenyl)-4,5-dihydro-1H-pyrazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 2.8 g. amount of sodium metal is dissolved in 200 ml. of absolute ethanol, then 21.35 g. of 3,4-dichlorophenylhydrazine hydrochloride is added followed in 10 minutes by 5.5 g. of acrylonitrile. The reaction mixture is refluxed for 4 hours then most of the ethanol is removed in vacuo. Water is added to separate a solid. The solid is collected by filtration and dried. The solid is dissolved in methanol, treated with activated charcoal and filtered. The filtrate is evaporated to give a solid. The solid is recrystallized from methanol to give the desired product as tan crystals, m.p. 182°-183.5° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. custommost of the ethanol is removed in vacuo
  3. additionWater is added
  4. customto separate a solid
  5. filtrationThe solid is collected by filtration
  6. customdried
  7. dissolutionThe solid is dissolved in methanol
  8. additiontreated with activated charcoal
  9. filtrationfiltered
  10. customThe filtrate is evaporated
  11. customto give a solid
  12. customThe solid is recrystallized from methanol

Sources & evidence

ORD record
ord-2d225caf103145379e09dab20467d6a6
Source dataset
uspto-grants-1984_05
Patent number
US04451479

Reaction notes

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