Dimethylformamide → 5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonyl chloride

HRID 1696732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696732
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].CN(C=O)C.[CH3:11][O:12][CH2:13][CH2:14][C:15]1[S:16][CH:17]=[CH:18][C:19]=1[CH3:20]>>[CH3:11][O:12][CH2:13][CH2:14][C:15]1[S:16][C:17]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:18][C:19]=1[CH3:20]

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24648Sulfuryl chlorideHCID 668571532-(2-Methoxy-ethyl)-3-methyl-thiophene

Produkt 1

HCID 866195455-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonyl chloride

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Sulfuryl chloride (0.26 g, 1.9 mmol) was added drop wise to a stirred solution of dry DMF (0.14 ml, 1.9 mmol) at 0° C. under an argon atmosphere resulting in the formation of a white solid. After 15 min, 2-(2-methoxy-ethyl)-3-methyl-thiophene (250 mg, 1.6 mmol) was added and the mixture was warmed to 100° C. and the melt was further stirred for 45 min. Crushed ice was added and the reaction mixture was extracted with ethyl acetate (2×) and the combined organic extracts were washed with water, brine, dried (magnesium sulfate. dihydrate), filtered and concentrated under reduced pressure. The crude solid was purified over silica gel (ethyl acetate/ n-heptane): light yellow oil, 220 mg, GC-MS (EI): M=254.

Aufarbeitung

  1. customresulting in the formation of a white solid
  2. additionCrushed ice was added
  3. extractionthe reaction mixture was extracted with ethyl acetate (2×)
  4. washthe combined organic extracts were washed with water, brine
  5. dry with materialdried (magnesium sulfate. dihydrate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude solid was purified over silica gel (ethyl acetate/ n-heptane)

Quellen und Nachweise

ORD-Eintrag
ord-b0b27ca882c74ac9b717db4833529cb4
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163778B2

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