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

HRID 727387

反応式

HRID 727387 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 65911,1,2,2-Tetrachloroethane溶媒

実験手順

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 C24N14O2N3Cl5 : C, 52.06; H, 2.55; N, 7.59. Found: C, 52.11; H, 2.57; N, 7.27.

後処理

  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

出典と根拠

ORDレコード
ord-00aff6261ec046d3a6549c48b117080f
出典データセット
uspto-grants-1998_01
特許番号
US05712303

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