Hydrochloric Acid → 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carbohydrazide

HRID 1867562Notes

Reaction equation

HRID 1867562 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]=[C:11]([C:22]([NH:24][NH:25]C(OC(C)(C)C)=O)=[O:23])[C:10]=2[CH3:33])=[CH:5][CH:4]=1>CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[N:12]=[C:11]([C:22]([NH:24][NH2:25])=[O:23])[C:10]=2[CH3:33])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86618350tert-Butyl 2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl]carbonyl]hydrazinecarboxylate

Product 1

HCID 109821545-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carbohydrazideYield 82.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

20 ml of 2N ethereal hydrochloric acid are added to a solution of 6.2 g of the compound obtained in stage B in 100 ml of MeOH and then the mixture is heated at 40° C. for 3 hours. The reaction mixture is concentrated under vacuum, the residue is extracted with ether, the organic phase is washed twice with a 10% NaHCO3 solution and dried over MgSO4, and the solvent is evaporated under vacuum. The residue is taken up in pentane and the precipitate formed is filtered off. 4.09 g of the expected compound are obtained.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. extractionthe residue is extracted with ether
  3. washthe organic phase is washed twice with a 10% NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated under vacuum
  6. customthe precipitate formed
  7. filtrationis filtered off

Sources & evidence

ORD record
ord-c06cd43da6e04963bf8faca7d93108f7
Source dataset
uspto-grants-2009_12
Patent number
US07632852B2

Reaction notes

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