2-(Trichloroacetyl)pyrrole → 2,2,2-trichloro-1-{4-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-1H-pyrrol-2-yl}-1-ethanone

HRID 494320노트

반응식

HRID 494320 반응식
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][C:25](F)=[CH:24][CH:23]=2)[C:18]=1[C:29](Cl)=[O:30]>C(Cl)Cl.[N+](C)([O-])=O>[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]=1[C:29]([C:8]1[CH:9]=[C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:10])[Cl:11])[NH:6][CH:7]=1)=[O:30]

참가 물질

6

반응물 3

HCID 3214872-(Trichloroacetyl)pyrroleHCID 27807113-(4-Fluorophenyl)-5-methyl-4-isoxazolecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 27685552,2,2-trichloro-1-{4-[(5-methyl-3-phenyl-4-isoxazolyl)carbonyl]-1H-pyrrol-2-yl}-1-ethanone수율 73.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매2회HCID 6375Nitromethane용매

실험 절차

To a solution of 2.1 g (10 mmol) of 2-trichloroacetyl-1H-pyrrole (commercially available) in CH2Cl2 (35 mL) and nitromethane (17.5 mL), 1.66 g (12.5 mmol) of AlCl3 was added in one portion. Then 2.96 g (12.5 mmol) of 5-methyl-3-(4-fluoro-phenyl)-isoxazole-4-carboxylic acid chloride (example 2, step 1) in 5 mL of CH2Cl2 was added dropwise. The reaction mixture was stirred at room temperature for 18 h before poured onto ice-water. The organic phase was separated, and the aqueous phase was extracted with diethyl ether. The combined organic solution was dried over Na2SO4, and evaporated to dryness. The obtained solid was washed extensively with petroleum ether to give 2.93 g 4-(5-methyl-3-phenyl-isoxazole-4-carbonyl)-2-trichloroacetyl-1H-pyrrole in 70% yield as yellow solid. (m/e): 414.8 (M+; 100%).

후처리

  1. additionbefore poured onto ice-water
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with diethyl ether
  4. dry with materialThe combined organic solution was dried over Na2SO4
  5. customevaporated to dryness
  6. washThe obtained solid was washed extensively with petroleum ether

출처 및 근거

ORD 기록
ord-6434b4eb4e2b4fccb1953b466f27fd6a
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538132B2

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