Acetyl chloride → 1-Ethyl-5-acetyloxindole

HRID 236377

반응식

HRID 236377 반응식
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[CH2:18]([N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29])[CH3:19]>>[CH2:18]([N:20]1[C:28]2[C:23](=[CH:24][C:25]([C:1](=[O:3])[CH3:2])=[CH:26][CH:27]=2)[CH2:22][C:21]1=[O:29])[CH3:19]

참가 물질

5

반응물 4

HCID 6367Acetyl chlorideHCID 7416NitrobenzeneHCID 66135N-EthyloxindoleHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 137705311-Ethyl-5-acetyloxindole수율 57.3%

반응 조건

온도
45 °C

실험 절차

To a mixture of 29.25 g. (0.373 mole) of acetyl chloride and 65.9 g. of aluminum chloride in 60 ml. of nitrobenzene was added gradually 20.0 (0.124 mole) of 1-ethyloxindole. The reaction warmed to about 45° C. with an evolution of gas. After stirring for one hour the reaction was heated to 100° C. for one hour and allowed to stir at room temperature over night. The reaction mixture was poured into 2 l. of ice with stirring. After 30 minutes the product was filtered, air dried and dissolved in 200 ml. of methylene chloride. The solution was dried over magnesium sulfate and concentrated to dryness. The residue was recrystallized from toluene, 14.44 g. (57.3% yield), m.p. 141°-145° C.

후처리

  1. additionTo a mixture of 29.25 g
  2. temperaturewas heated to 100° C. for one hour
  3. stirringto stir at room temperature over night
  4. additionThe reaction mixture was poured into 2 l
  5. stirringof ice with stirring
  6. filtrationAfter 30 minutes the product was filtered
  7. customair dried
  8. dissolutiondissolved in 200 ml
  9. dry with materialThe solution was dried over magnesium sulfate
  10. concentrationconcentrated to dryness
  11. customThe residue was recrystallized from toluene, 14.44 g

출처 및 근거

ORD 기록
ord-cd5efd8eaf214fefa25af3f3f35f904d
출처 데이터셋
uspto-grants-1987_02
특허 번호
US04644005

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