Chloroacetyl chloride → 5-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one

HRID 365367ノート

反応式

HRID 365367 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][C:7](Cl)=[O:8].[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][C:11]1=[O:19]>C(=S)=S>[Cl:5][CH2:6][C:7]([C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11](=[O:19])[CH2:12]2)=[O:8]

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 321710OxindoleHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 20605765-(Chloroacetyl)-1,3-dihydro-2H-indol-2-one収率 98.9%

試薬・触媒・溶媒 1

HCID 6348Carbon Disulfide溶媒

実験手順

To a 250 ml round-bottomed flask equipped with condenser and nitrogen inlet were added 30.7 grams (230 mmol) aluminum chloride, 150 ml carbon disulfide, and 3.8 ml (48 mmol) chloroacetyl chloride. To the stirring mixture was added 5.0 grams (37 mmol) of oxindole portionwise over 15 minutes. The reaction was stirred a further 10 minutes, then refluxed 2 hours. The reaction was cooled, added to ice, stirred thoroughly, and the beige precipitate filtered, washed with water, and dried to afford 7.67 grams (97%) of 5-chloroacetyl-oxindole. NMR (d, DMSO-d6): 3.40 (s, 2H), 5.05 (s, 2H), 6.8-7.9 (m, 3H).

後処理

  1. customTo a 250 ml round-bottomed flask equipped with condenser and nitrogen inlet
  2. temperaturerefluxed 2 hours
  3. temperatureThe reaction was cooled
  4. additionadded to ice
  5. stirringstirred thoroughly
  6. filtrationthe beige precipitate filtered
  7. washwashed with water
  8. customdried

出典と根拠

ORDレコード
ord-077f193df9814c5b8f2391f696c97e56
出典データセット
uspto-grants-2000_10
特許番号
US06127373

反応ノート

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