Methyl iodide → Methyl 2-(3-methoxybenzylthio)nicotinate

HRID 35530

Reaktionsgleichung

Reaktionsgleichung von HRID 35530
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].[CH3:20]I>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][S:7][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([O:12][CH3:20])=[O:11]

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 8593402-(3-Methoxybenzylthio)nicotinic acid

Produkt 1

HCID 14277645Methyl 2-(3-methoxybenzylthio)nicotinateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A suspension of 7.15 g (0.026 mole) of 2-(3-methoxybenzylthio)nicotinic acid in 75 ml of dry acetonitrile was treated with 3.95 g (0.026 mole) of 1,8-diazabicyclo[5,4,0]-under-7-ene (DBU). A solution formed and 4.26 g (0.030 mole) of methyl iodide was added over one minute. After keeping the reaction mixture at room temperature for 24 hours, the solution was evaporated in vacuo. The residue was partitioned between 100 ml of ether and 50 ml of water. The ether layer was washed with 50 ml of H2O, dried, and evaporated to a small volume. The addition of hexane with cooling yielded 6.9 g (92% of theory) of methyl 2-(3-methoxybenzylthio)nicotinate; m.p. 69°-70° C.

Aufarbeitung

  1. customA solution formed
  2. customat room temperature
  3. customfor 24 hours
  4. customthe solution was evaporated in vacuo
  5. customThe residue was partitioned between 100 ml of ether and 50 ml of water
  6. washThe ether layer was washed with 50 ml of H2O
  7. customdried
  8. customevaporated to a small volume
  9. additionThe addition of hexane
  10. temperaturewith cooling

Quellen und Nachweise

ORD-Eintrag
ord-ee89b9311b3e4966b2625b4cea6c2b1c
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04767766

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