Water → 1H-Pyrrole-3-carbonitrile, 2-(4-chlorophenyl)-4,5-bis(trifluoromethyl)-

HRID 974406ノート

反応式

HRID 974406 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=O)O[C:10]([C:14]([F:17])([F:16])[F:15])=[N:9]2)=[CH:4][CH:3]=1.Br/C(=[CH:22]\[C:23]([F:26])([F:25])[F:24])/C#N.[CH2:27]([N:29](CC)CC)C.O>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[C:22]([C:23]([F:26])([F:25])[F:24])[C:12]=2[C:27]#[N:29])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 157530294-(p-Chlorophenyl)2-trifluoromethyl-2-oxazolin-5-oneHCID 218608782-Bromo-4,4,4-trifluorocrotononitrile

生成物 1

HCID 110242451H-Pyrrole-3-carbonitrile, 2-(4-chlorophenyl)-4,5-bis(trifluoromethyl)-収率 91.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
25 °C

実験手順

4-(p-Chlorophenyl)-2-(trifluoromethyl)-2-oxazolin-5-one (2.0 g, 7.59 mmol) and 2-bromo-4,4,4-trifluorocrotononitrile (0.81 g, 4.05 mmol) are dissolved in acetonitrile (10 mL). To the resulting yellow solution triethylamine (0.45 g, 4.46 mmol) is added dropwise while the reaction flask is cooled with a water bath. After stirring at 25° C. overnight, the reaction mixture is poured into water. The aqueous layer is extracted with ethyl acetate and the combined organic extracts are washed sequentially with water, 5% sodium thiosulfate solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give a yellow solid. The solid is chromatographed using silica gel and eluted with hexane/ethyl acetate 3:1 to yield the title compound as yellow crystals (1.26 g, mp 208° C.)

後処理

  1. temperatureis cooled with a water bath
  2. extractionThe aqueous layer is extracted with ethyl acetate
  3. washthe combined organic extracts are washed sequentially with water, 5% sodium thiosulfate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid
  7. customThe solid is chromatographed
  8. washeluted with hexane/ethyl acetate 3:1

出典と根拠

ORDレコード
ord-74fd8a50111f4d2f955966fba0b3d870
出典データセット
uspto-grants-1991_11
特許番号
US05068390

反応ノート

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