Hydrochloric Acid → 6-Fluoroisatin

HRID 2174204노트

반응식

HRID 2174204 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].O.Cl[C:11](Cl)(Cl)[CH:12]=[O:13].Cl.ON.S([O-])([O-])(=O)=[O:20].[Na+].[Na+].Cl>O>[F:1][C:2]1[CH:3]=[C:4]2[C:6]([C:12](=[O:13])[C:11](=[O:20])[NH:5]2)=[CH:7][CH:8]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 97423-FluoroanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 205283762,2,2-Trichloroacetaldehyde hydrate

생성물 1

HCID 3739056-Fluoroisatin수율 55.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

9.6 g of 3-fluoroaniline were added to 590 mL of water followed by the addition of 17.2 g of trichloroacetaldehyde monohydrate, 21.9 g of hydroxyamine hydrochloride and 98.2 g of anhydrous sodium sulfate and stirring the mixture for 5 hours at 50° C. After cooling the resultant to room temperature and allowing to stand overnight, 31 mL of 2 N HCl were added thereto followed by stirring the mixture for 30 minutes and then filtering out the crystals. After drying the resulting crystals, the crystals were added to concentrated sulfuric acid heated to 70° C., followed by stirring the mixture for 1 hour at 80° C. to 90° C. The reaction mixture was poured over ice followed by extracting with ethyl acetate and washing with saturated saline. After drying the organic layer with magnesium sulfate, the solvent was distilled off under reduced pressure to obtain 7.96 g of a crude product of 6-fluoroisatin.

후처리

  1. temperatureAfter cooling the resultant to room temperature
  2. waitto stand overnight
  3. stirringby stirring the mixture for 30 minutes
  4. filtrationfiltering out the crystals
  5. customAfter drying the resulting crystals
  6. additionthe crystals were added to concentrated sulfuric acid
  7. temperatureheated to 70° C.
  8. stirringby stirring the mixture for 1 hour at 80° C. to 90° C
  9. additionThe reaction mixture was poured over ice
  10. extractionby extracting with ethyl acetate
  11. washwashing with saturated saline
  12. dry with materialAfter drying the organic layer with magnesium sulfate
  13. distillationthe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-c7705bb9dc7b4dadaafb843cfd2b0be9
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09060517B2

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