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

HRID 217709
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 217709
[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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

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

Produkt 1

HCID 452578932-Bromo-1-[3-methylamino-5-(pentafluorosulfanyl)phenyl]ethanoneAusbeute 44,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857
Ethyl Acetate
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-[3-(2-Bromoacetyl)-5-(pentafluoro sulfanyl)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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8f8915b7ff364463b678b06ec4fe6dab
Quelldatensatz
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08198272B2

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