Trichloroacetyl chloride → 4-(trichloroacetyl)-1H-pyrrole-2-carbonitrile

HRID 73655노트

반응식

HRID 73655 반응식
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](Cl)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3].[C:12]([C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1)#[N:13]>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]([Cl:7])([Cl:6])[C:3]([C:17]1[CH:18]=[C:14]([C:12]#[N:13])[NH:15][CH:16]=1)=[O:4]

참가 물질

6

반응물 3

HCID 6420Trichloroacetyl chlorideHCID 138277Pyrrole-2-carbonitrileHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 124151024-(trichloroacetyl)-1H-pyrrole-2-carbonitrile수율 100.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매3회HCID 8857Ethyl Acetate용매

실험 절차

Trichloracetyl chloride (44.4 g, 27.3 mL, 244 mmol) in dichloromethane (75 mL) was added over 20 min to a mechanically stirred suspension of aluminum trichloride (54.3 g, 407 mmol) in dichloromethane (150 mL). The resulting mixture was stirred for 30 min, and then 2-cyanopyrrole (15.0 g, 163 mmol) in dichloromethane (75 mL) was added over 30 min. The reaction was heated at reflux for 5 h and then allowed to cool. The reaction was diluted with ethyl acetate (600 mL) and then quenched slowly with water (300 mL). The layers were separated and then the organic layer was washed with water and brine, dried (magensium sulfate) and evaporated under reduced pressure to afford a quantitative yield of desired product (39.0 g, 100%) containing trace impurities. This material was used in the next step without further purification. 1H NMR (DMSO-d6) δ 8.14 (s, 1H), 7.55 (s, 1H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 5 h
  3. temperatureto cool
  4. customquenched slowly with water (300 mL)
  5. customThe layers were separated
  6. washthe organic layer was washed with water and brine
  7. dry with materialdried (magensium sulfate)
  8. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-567ac49590a44c5288b0f8201afa293a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829185B2

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