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

HRID 365367노트

반응식

HRID 365367 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-077f193df9814c5b8f2391f696c97e56
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127373

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