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Water → 2-Bromo-1-[3-methylamino-5-(pentafluorosulfanyl)phenyl]ethanone

HRID 657932
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HRID 657932 반응식
[Br:1][CH2:2][C:3]([C:5]1[CH:6]=[C:7]([N:17](C)[C:18](=O)C(F)(F)F)[CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)=[O:4].O.S(=O)(=O)(O)O.[OH-].[Na+]>CC(=O)OCC>[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([S:11]([F:16])([F:12])([F:13])([F:14])[F:15])[CH:8]=[C:7]([NH:17][CH3:18])[CH:6]=1)=[O:4]
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참가 물질

6

반응물 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 58136859HCID 58136859, 화합물

생성물 1

HCID 452578932-Bromo-1-[3-methylamino-5-(pentafluorosulfanyl)phenyl]ethanone수율 44.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate
용매

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온도
80 °C

실험 절차

N-[3-(2-Bromoacetyl)-5-(pentafluorosulfanyl)phenyl]-2,2,2-trifluoro-N-methylacetamide (O1.075; 1.2 g) was admixed with water (15 ml), and concentrated sulfuric acid (15 ml) was added dropwise while stirring and with ice cooling. The mixture was heated to 80° C. and stirred at this temperature for 7 h. After cooling, the reaction mixture was added slowly to a mixture of 10 N sodium hydroxide solution and EA, and the aqueous phase was extracted five times with EA. The combined organic phases were dried over magnesium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. The residue was purified by means of preparative HPLC (met. A). The product fractions, each of them clean, were combined, freed of the acetonitrile under reduced pressure, neutralized with sodium hydrogencarbonate and extracted three times with EA. The combined organic phases were dried over magnesium sulfate and, after the desiccant had been filtered off, dried under reduced pressure. 420 mg of the title compound were isolated.

후처리

  1. additionwas added dropwise
  2. stirringstirred at this temperature for 7 h
  3. temperatureAfter cooling
  4. extractionthe aqueous phase was extracted five times with EA
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationafter the desiccant had been filtered off
  7. customdried under reduced pressure
  8. customThe residue was purified by means of preparative HPLC (
  9. extractionextracted three times with EA
  10. dry with materialThe combined organic phases were dried over magnesium sulfate
  11. filtrationafter the desiccant had been filtered off
  12. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-4aa2d7adc0514899a43fea08992dce6f
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08076336B2

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