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3-Thiophencarboxamide,N-methyl- → HCID 10244631, Verbindung

HRID 1437141
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1437141
[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][CH:6]=1)=[O:4].O[CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15]>S(=O)(=O)(O)O.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH3:1][NH:2][C:3]([C:5]1[CH:9]=[C:8]([CH2:11][NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])[S:7][CH:6]=1)=[O:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 8195533-Thiophencarboxamide,N-methyl-HCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

Produkt 1

HCID 10244631HCID 10244631, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1118Sulfuric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel
HCID 516892
Sodium Bicarbonate
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To suspension of N-methyl-3-thiophenecarboxamide (1.12 g) (prepared according to J. Org. Chem. (1976), 41(23), 3668-74) in concentrated aqueous sulphuric acid (25 ml) at 0-5° C. was added N-(hydroxymethyl)trifluoroacetamide (1.134 g). The suspension was allowed to warm to 20° C. and stirred for 2 h. The mixture was poured onto ice (150 g) and diluted with ethyl acetate (200 ml). The biphase mixture was diluted with saturated sodium hydrogen carbonate (200 ml) and treated with sodium hydrogen carbonate (21 g). The phases were separated and the organic phase washed with saturated sodium hydrogen carbonate (150 ml×2). The combined aqueous phases were extracted with ethyl acetate (100 ml). The combined organic extracts were concentrated in vacuo. The residue was pre-absorbed onto silica and purified by biotage (90 g) eluting with 1:1 to 0:1 cyclohexane:ethyl acetate to give the title compound as a white solid (0.7129).

Aufarbeitung

  1. additionThe mixture was poured onto ice (150 g)
  2. customThe phases were separated
  3. washthe organic phase washed with saturated sodium hydrogen carbonate (150 ml×2)
  4. extractionThe combined aqueous phases were extracted with ethyl acetate (100 ml)
  5. concentrationThe combined organic extracts were concentrated in vacuo
  6. customThe residue was pre-absorbed onto silica
  7. custompurified by biotage (90 g)
  8. washeluting with 1:1 to 0:1 cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-be5173694d8d4c139d62c84e87399bc1
Quelldatensatz
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07622464B2

Notizen zur Reaktion

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