Methanol → Methyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate

HRID 377636Notes

Reaction equation

HRID 377636 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]([OH:23])=[O:22])[C:9]=2[CH3:24])=[CH:4][CH:3]=1.[CH3:25]O>>[Cl:1][C:2]1[CH:3]=[CH:4][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]([O:23][CH3:25])=[O:22])[C:9]=2[CH3:24])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 887MethanolHCID 15194215-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid

Product 1

HCID 19356244Methyl 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylate

Procedure

19.54 g of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid are dissolved in 350 ml of MeOH, 0.97 g of paratoluenesulfonic acid is added and the mixture is then refluxed for 18 hours. After evaporation of the solvent, the residue is taken up with AcOEt and washed with saturated NaHCO3 solution and then with saturated NaCl solution. It is dried over MgSO4, the insoluble material is filtered off and the filtrate is then concentrated to dryness to give 18.53 g of the expected compound, m.p.=133° C.

Workup

  1. temperaturethe mixture is then refluxed for 18 hours
  2. customAfter evaporation of the solvent
  3. washwashed with saturated NaHCO3 solution
  4. dry with materialIt is dried over MgSO4
  5. filtrationthe insoluble material is filtered off
  6. concentrationthe filtrate is then concentrated to dryness

Sources & evidence

ORD record
ord-5d15404827ee44daa2120a4c7c345c9c
Source dataset
uspto-grants-2000_02
Patent number
US06028084

Reaction notes

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