Sodium Carbonate → 2-((6-Methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetic acid

HRID 72649

Reaktionsgleichung

Reaktionsgleichung von HRID 72649
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][S:10]([CH2:13][C:14]([O-:16])=[O:15])(=[O:12])=[O:11])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>O.CO>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][S:10]([CH2:13][C:14]([OH:16])=[O:15])(=[O:12])=[O:11])=[CH:5][C:4]=1[N+:17]([O-:19])=[O:18]

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 67994885HCID 67994885, Verbindung

Produkt 1

HCID 679948792-((6-Methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetic acidAusbeute 98,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 2-((6-methoxy-5-nitropyridin-3-yl)methylsulfonyl)acetate (1.83 g, 6 mmol) and sodium carbonate (1.8 g, 15 mmol) in a mixture of water (10 mL) and methanol (10 mL) was stirred at room temperature for 4 hours. After evaporated to dryness, the residue was acidized by dropwise addition of 1N aq. HCl. White solid was precipitated gradually as pH was brought to 2 and filtrated to give the pure product (1.72 g, 98.7%). M.p. 183-186° C.; 1H-NMR (DMSO-d6): δ 4.06 (s, 3H, OCH3), 4.13 (s, 2H, CH2), 4.79 (s, 2H, CH2), 8.48 (d, 1H J=2.0 Hz, Py-H), 8.50 (d, 1H, J=2.0 Hz, Py-H); 13C-NMR (DMSO-d6): δ 55.07, 55.41, 57.15, 118.45, 133.64, 137.96, 154.26, 156.23, 164.88; HR-MS (ESI+) m/z: 289.0064 [M+H]+; C9H10N2O7S requires 290.0209

Aufarbeitung

  1. customAfter evaporated to dryness
  2. additionthe residue was acidized by dropwise addition of 1N aq. HCl
  3. customWhite solid was precipitated gradually as pH
  4. filtrationfiltrated

Quellen und Nachweise

ORD-Eintrag
ord-dcb7d44e2b8a44259ad7ba17e15535d8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829003B2

Verknüpfte Notizen

Wird geladen…