2-Chloro-5-(chloromethyl)pyridine → 2-Chloro-5-[(methylthio)methyl]pyridine

HRID 646625

Reaktionsgleichung

Reaktionsgleichung von HRID 646625
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[N:7][CH:8]=1.[CH3:10][S-:11].[Na+]>C(O)C>[Cl:9][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][S:11][CH3:10])=[CH:8][N:7]=1

Komponenten

4

Edukt 2

HCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 4378561Sodium methanethiolate

Produkt 1

HCID 206703602-Chloro-5-[(methylthio)methyl]pyridineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 5-chloromethyl-2-chloropyridine (8.1 g, 50 mmol) in ethanol (50 mL) was added to a suspension of sodium thiomethoxide solid (4.2 g, 60 mmol) in 100 mL ethanol under stirring. An exothermic reaction was observed during the addition and the mixture was then stirred at room temperature overnight. The solvent ethanol was removed under reduced pressure and the residue was re-dissolved in ether-EtOAc solvent and mixed with brine. The two phases were separated and the organic layer was dried over anhydrous Na2SO4, filtered, concentrated and purified by eluting through a silica gel plug with 40% EtOAc in hexane to give 8.14 g of 2-chloro-5-[(methylthio)methyl]pyridine (A) as a colorless oil in 94% yield. The product was analytically pure and directly used for the next step reaction. 1H NMR (300 MHz, CDCl3) δ 8.28 (dd, 1H), 7.65 (dd, 1H), 7.30 (d, 1H), 3.63 (s, 2H), 2.00 (s, 3H).

Aufarbeitung

  1. customAn exothermic reaction
  2. additionwas observed during the addition
  3. stirringthe mixture was then stirred at room temperature overnight
  4. customThe solvent ethanol was removed under reduced pressure
  5. dissolutionthe residue was re-dissolved in ether-EtOAc solvent
  6. additionmixed with brine
  7. customThe two phases were separated
  8. dry with materialthe organic layer was dried over anhydrous Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. custompurified
  12. washby eluting through a silica gel plug with 40% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-c9786705c76e4985a4dbafe53a4a4b13
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07705156B2

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