Hydrazine hydrate (1:1) → 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carbohydrazide

HRID 2374452Notes

Reaction equation

HRID 2374452 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21](Cl)=[O:22])[C:9]=2[CH3:24])=[CH:4][CH:3]=1.O.[NH2:26][NH2:27]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:26][NH2:27])=[O:22])[C:9]=2[CH3:24])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 152841395-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carbonyl chloride

Product 1

HCID 109821545-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carbohydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 g of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carbonyl chloride in 100 ml of ethanol are placed under nitrogen and the mixture is heated at reflux for 2 hours. It is allowed to return to a temperature of 20-25° C., then 50 g of hydrazine hydrate are added and the mixture is again heated at reflux for 3 and a half hours. The reaction medium is filtered while hot and then the ethanol is evaporated. The reaction medium is concentrated, then taken up in 150 ml of DCM and separated by settling. The aqueous phase is discarded, the organic phase is washed twice with 100 ml of water and then the DCM is evaporated. After drying under vacuum, 16.9 g of the expected compound are obtained.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 2 hours
  3. customto return to a temperature of 20-25° C.
  4. temperaturethe mixture is again heated
  5. temperatureat reflux for 3 and a half hours
  6. filtrationThe reaction medium is filtered while hot and then the ethanol
  7. customis evaporated
  8. concentrationThe reaction medium is concentrated
  9. customseparated
  10. washthe organic phase is washed twice with 100 ml of water
  11. customthe DCM is evaporated
  12. dry with materialAfter drying under vacuum, 16.9 g of the expected compound
  13. customare obtained

Sources & evidence

ORD record
ord-e76f4285cb0847fc885c32915e454412
Source dataset
uspto-grants-2008_12
Patent number
US07462632B2

Reaction notes

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