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Hydrochloric Acid → N-(3-Acetyl-5-pentafluorosulfanylphenyl)-N-ethyl-2,2,2-trifluoroacetamide

HRID 1258505
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1258505
[C:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].I[CH2:30][CH3:31].IC.Cl>C(COC)OC.C(OCC)(=O)C.O>[C:1]([C:4]1[CH:5]=[C:6]([N:16]([CH2:30][CH3:31])[C:17](=[O:22])[C:18]([F:21])([F:19])[F:20])[CH:7]=[C:8]([S:10]([F:14])([F:15])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 58085708HCID 58085708, Verbindung

Produkt 1

HCID 58137469N-(3-Acetyl-5-pentafluorosulfanylphenyl)-N-ethyl-2,2,2-trifluoroacetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

N-(3-Acetyl-5-pentafluorosulfanylphenyl)-2,2,2-trifluoroacetamide (100 mg, example 4d) was dissolved in absolute dimethoxyethane (5 ml) in a microwave insert and admixed with powdered potassium carbonate (40 mg). After adding iodoethane (60 μl), the mixture was heated to 100° C. in the microwave for 30 min. Subsequently, further iodomethane (60 μl) was added and the mixture was heated again to 100° C. for 30 min. This operation was repeated once more. Then the mixture was worked up by adding it to a mixture of water, ethyl acetate and 1 N HCl. Removal of the organic phase was followed by extraction three times more with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 50 mg of the desired compound were obtained.

Aufarbeitung

  1. temperaturethe mixture was heated again to 100° C. for 30 min
  2. additionby adding it
  3. customRemoval of the organic phase
  4. extractionwas followed by extraction three times more with ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by means of preparative HPLC
  9. extractionextracted three times with ethyl acetate
  10. dry with materialThe combined extracts were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7bec71f5bf274a7081dbb73ce36c7ede
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466169B2

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