Water → HCID 60735499, Verbindung

HRID 1942245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1942245
Cl[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1.[C:9]([O-])([O-])=O.[K+].[K+].C[CH:16]([SH:20])[C:17]([O-:19])=[O:18].O>CN(C=O)C>[CH3:9][O:19][C:17](=[O:18])[CH2:16][S:20][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 276852,5-DichloropyridineHCID 156077362-Mercaptopropionate

Produkt 1

HCID 60735499HCID 60735499, VerbindungAusbeute 76,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,5-dichloropyridine (13, 2.04 g, 13.8 mmol) in 40 mL of dry DMF was added K2CO3 (1.91 g, 13.8 mmol) and reaction mixture was stirred for 30 min at ambient temperature. Neat methylthioglycolate (1.26 mL, 14 mmol) was added via syringe and the reaction mixture was stirred overnight under N2. The reaction mixture was treated with H2O (120 mL) and the product was extracted into EtOAc (2×220 mL). Combined organic layers were washed with lot of water, brine, dried over Na2SO4, filtered and concentrated to give 2.3 g of crude material which was purified by column chromatography (hexanes/EtOAc). Obtained 1.1 g (5.0 mmol) of target 14, as a colorless oil, in 36% yield.

Aufarbeitung

  1. stirringthe reaction mixture was stirred overnight under N2
  2. extractionthe product was extracted into EtOAc (2×220 mL)
  3. washCombined organic layers were washed with lot of water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0e3097f0b611408fbb26b0a2fe17497e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389546B2

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