Benzoyl chloride → 1-Ethyl-5-benzoyloxindole

HRID 236364

反応式

HRID 236364 の反応式
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[CH2:23]([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27][C:26]1=[O:34])[CH3:24]>>[CH2:23]([N:25]1[C:33]2[C:28](=[CH:29][C:30]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:31][CH:32]=2)[CH2:27][C:26]1=[O:34])[CH3:24]

参加物

5

反応物 4

HCID 7412Benzoyl chlorideHCID 7416NitrobenzeneHCID 66135N-EthyloxindoleHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 137705251-Ethyl-5-benzoyloxindole収率 42.8%

反応条件

温度
100 °C

実験手順

To a mixture of 26.18 g. (186 mmoles) of benzoyl chloride and 32.95 g. of aluminum chloride in 30 ml. of nitrobenzene was gradually added 10.0 g. (62.1 mmoles) of 1-ethyloxindole. The reaction mixture was heated to 100° C. for one hour, cooled and added to 2 l. of ice-water with stirring. The mixture was extracted with methylene chloride (5×200 ml.) and the extracts dried over magnesium sulfate and concentrated in vacuo. The nitrobenzene was distilled from the residue under high vacuum and the residue treated with diethyl ether to induce crystallization. The resulting solids were filtered and recrystallized from methylene chloride petroleum ether, 7.05 g. (42.8% yield), m.p. 134°-136° C.

後処理

  1. additionTo a mixture of 26.18 g
  2. temperaturecooled
  3. additionadded to 2 l
  4. extractionThe mixture was extracted with methylene chloride (5×200 ml.)
  5. dry with materialthe extracts dried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationThe nitrobenzene was distilled from the residue under high vacuum
  8. additionthe residue treated with diethyl ether
  9. customcrystallization
  10. filtrationThe resulting solids were filtered
  11. customrecrystallized from methylene chloride petroleum ether, 7.05 g

出典と根拠

ORDレコード
ord-a5ad2194f2064de188c0df6f18533e41
出典データセット
uspto-grants-1987_02
特許番号
US04644005

関連ノート

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