Potassium Carbonate → Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate

HRID 72660

Reaktionsgleichung

Reaktionsgleichung von HRID 72660
Br[CH2:2][C:3]1[N:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH3:13])=[CH:5][CH:4]=1.C[CH:15]([SH:19])[C:16]([O-:18])=[O:17].[C:20](=O)([O-])[O-].[K+].[K+]>CO>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][S:19][CH2:15][C:16]([O:18][CH3:20])=[O:17])=[N:8][C:7]=1[N+:9]([O-:11])=[O:10]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 144051243-Methoxy-2-nitro-6-pyridylmethyl bromideHCID 156077362-Mercaptopropionate

Produkt 1

HCID 67994824Methyl 2-((5-methoxy-6-nitropyridin-2-yl)methylthio)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 6-(bromomethyl)-3-methoxy-2-nitropyridine (30 mmol, 0.74 g), methythioglycolate (2.7 mL, 30 mmol), and potassium carbonate (5.5 g, 40 mmol) in methanol (200 mL) was stirred at room temperature for 10 hours. After concentrated the mixture was purified by column chromatography using PE/DCM (1:1, v/v) followed by DCM to the titled compound. 1H-NMR (CDCl3): δ 3.27 (S, 2H, CH2), 3.74 (S, 3H, OCH3), 3.93 (S, 2H, CH2), 3.99 (S, 3H, OCH3), 7.51 (d, 1H, J=8.6 Hz, Py-H), 7.65 (d, 1H, J=8.6 Hz, Py-H); HR-MS (ESI+) m/z 272.0467 [M+H]+ C10H12N2O5S requires 273.0547.

Aufarbeitung

  1. concentrationAfter concentrated the mixture
  2. customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-41f55f15631d41559d11993553177430
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829003B2

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