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

HRID 1907828
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HRID 1907828 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 cooling with ice. The mixture was heated to 80° C. and stirred at this temperature for 7 h. After cooling, the reaction mixture was slowly added to a mixture of 10N 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 filtering off the desiccant under reduced pressure, dried. The residue was purified by means of preparative HPLC. 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 filtering off the desiccant, dried under reduced pressure. 420 mg of the title compound were isolated. LC-MS Rt: 1.64 min [M+H]+:354.0

후처리

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

출처 및 근거

ORD 기록
ord-38e4fc5bc95d41358b1269b730f6ea89
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08598177B2

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