3-Methylsulfanyl-5-trifluoromethyl-1,3-dihydro-indol-2-one → 5-(Trifluoromethyl)oxindole

HRID 743156노트

반응식

HRID 743156 반응식
CS[CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[NH:5][C:4]1=[O:16]>CC(O)=O.[Zn]>[F:15][C:12]([F:13])([F:14])[C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:16])[CH2:3]2

참가 물질

4

반응물 1

HCID 123514913-Methylsulfanyl-5-trifluoromethyl-1,3-dihydro-indol-2-one

생성물 1

HCID 37344575-(Trifluoromethyl)oxindole수율 90%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 176Acetic Acid용매

실험 절차

A solution of 3-(methylthio)-5-(trifluoromethyl)oxindole (Gassman PG, Cue BW, Luh T-Y, J. Org. Chem. 1977;42:1344-1348) (10 g, 40 mmol) in AcOH (100 mL) was heated under reflux with Zn dust (13.3 g, 0.2 mol) for 1 hour. The mixture was cooled and filtered, and the precipitate was washed with AcOH. The combined filtrates were evaporated under reduced pressure, and the residue was diluted with 1M aqueous ammonia to give 5-trifluoromethyloxindole [VII: R1 =5-CF3, R3 =H] (7.22 g, 90%); mp (aqueous EtOH) 188.5°-191° C. (lit. [Hardtmann GE, U.S. Pat. No. 4,160,032; Chem. Abstr. 1979;91:P107890w]; mp 188°-189° C.).

후처리

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe precipitate was washed with AcOH
  4. customThe combined filtrates were evaporated under reduced pressure
  5. additionthe residue was diluted with 1M aqueous ammonia

출처 및 근거

ORD 기록
ord-bf7a2b1700d443f897eaeb438845b4bd
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556874

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