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

HRID 494320ノート

反応式

HRID 494320 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 6375Nitromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-6434b4eb4e2b4fccb1953b466f27fd6a
出典データセット
uspto-grants-2009_05
特許番号
US07538132B2

反応ノート

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