2-Chlorobenzoyl chloride → 5-(2-Chlorobenzamido)-4-(2-chlorobenzoyl)-3-methyl-1-(2,4,6-trichlorophenyl)pyrazole

HRID 1871611Notes

Reaction equation

HRID 1871611 reaction equation
[Cl-:1].[Cl-].[Cl-].[Al+3].[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8](Cl)=[O:9].[NH2:15][C:16]1[N:20]([C:21]2[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=2[Cl:29])[N:19]=[C:18]([CH3:30])[CH:17]=1>ClC(Cl)C(Cl)Cl>[Cl:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([NH:15][C:16]1[N:20]([C:21]2[C:26]([Cl:27])=[CH:25][C:24]([Cl:28])=[CH:23][C:22]=2[Cl:29])[N:19]=[C:18]([CH3:30])[C:17]=1[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[Cl:1])=[O:9]

Participants

5

Reactant 3

HCID 691102-Chlorobenzoyl chlorideHCID 20600323-Methyl-1-(2,4,6-trichlorophenyl)-1H-pyrazol-5-amineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 184277925-(2-Chlorobenzamido)-4-(2-chlorobenzoyl)-3-methyl-1-(2,4,6-trichlorophenyl)pyrazoleYield 51.2%

Reagents, catalysts & solvents 1

HCID 65911,1,2,2-TetrachloroethaneSolvent

Procedure

A suspension of 2.34 g (17.50 mmol) of aluminum trichloride in 20 mL of 1,1,2,2-tetrachloroethane was treated with 2.02 mL (2.78 g, 15.9 mmol) of 2-chlorobenzoyl chloride and the resulting solution was stirred for 20 minutes at room temperature. Then 2.00 g (7.23 mmol) of the product of Step A was added and the reaction mixture was refluxed for 16 hours. The cooled reaction mixture was poured over ice and the insolubles were filtered off and washed with ethyl acetate. The organic layer was separated and the aqueous was washed twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The residues were chromatographed on silica gel, eluting with 4:1 hexane ethyl acetate to give 2.05 g (51%) of the title product, an amorphous foam. Anal. Calcd. for C24H14O2N3Cl5 : C, 52.06; H, 2.55; N, 7.59. Found: C, 52.11; H, 2.57; N, 7.27.

Workup

  1. temperaturethe reaction mixture was refluxed for 16 hours
  2. customThe cooled reaction mixture
  3. additionwas poured over ice
  4. filtrationthe insolubles were filtered off
  5. washwashed with ethyl acetate
  6. customThe organic layer was separated
  7. washthe aqueous was washed twice with ethyl acetate
  8. dry with materialThe combined organic layers were dried over magnesium sulfate
  9. customevaporated
  10. customThe residues were chromatographed on silica gel
  11. washeluting with 4:1 hexane ethyl acetate

Sources & evidence

ORD record
ord-eda38d0d8c7b44b381ecbb1e134e1a2d
Source dataset
uspto-grants-2000_08
Patent number
US06103900

Reaction notes

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