Indole → 3-(methylthio)-1H-indole

HRID 1947065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947065
[S:1]([CH3:3])[CH3:2].ClN1C(=O)CCC1=O.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)C=[CH:13]1.CCOCC>C(Cl)Cl>[CH3:2][S:1][C:3]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[NH:12][CH:13]=1

Komponenten

6

Edukt 4

HCID 798IndoleHCID 1068Dimethyl SulfideHCID 3283Diethyl EtherHCID 31398Chlorosuccinimide

Produkt 1

HCID 108882523-(methylthio)-1H-indoleAusbeute 98,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Me2S (955 μL, 13 mmol) was added to a solution of N-chlorosuccinimide (NCS, 1.47 g, 11 mmol) in DCM (80 mL) at 0° C., and stirred under N2 for 35 min. A solution of indole (1.17 g, 10 mmol) in DCM was added slowly, stirring at 0° C. for 2 h. While still cold, Et2O was added, and the white gum that formed was filtered off, dried under vacuum for 1.5 h, and stored at RT overnight. The intermediate was dissolved in DMSO, and the mixture heated to 100° C. under vacuum for 25 min. The product was poured into water, extracted with Et2O, and concentrated to dryness to yield 3-methylsulfanyl-1H-indole (1.609 g, 98.6% yield).

Aufarbeitung

  1. stirringstirring at 0° C. for 2 h
  2. customthe white gum that formed
  3. filtrationwas filtered off
  4. customdried under vacuum for 1.5 h
  5. waitstored at RT overnight
  6. dissolutionThe intermediate was dissolved in DMSO
  7. additionThe product was poured into water
  8. extractionextracted with Et2O
  9. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-cc063adc5c9640319a1b2129781a3176
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399462B2

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