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

HRID 974406노트

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HRID 974406 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
25 °C

실험 절차

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.)

후처리

  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

출처 및 근거

ORD 기록
ord-74fd8a50111f4d2f955966fba0b3d870
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068390

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