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

HRID 727387

반응식

HRID 727387 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 65911,1,2,2-Tetrachloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-00aff6261ec046d3a6549c48b117080f
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05712303

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