Methyl iodide → Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamate

HRID 2197423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2197423
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12](=[O:18])[NH:13][CH:14]=[C:15]([I:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:21]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C:11]1[C:12]([O:18][CH3:21])=[N:13][CH:14]=[C:15]([I:17])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 6328Methyl iodideHCID 10044624Benzyl 5-iodo-2-oxo-1,2-dihydropyridin-3-ylcarbamate

Produkt 1

HCID 59432848Benzyl (5-iodo-2-methoxypyridin-3-yl)carbamateAusbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

(5-Iodo-2-oxo-1,2-dihydro-pyridin-3-yl)-carbamic acid benzyl ester (3.68 g, 9.94 mmol) was dissolved in chloroform (50 mL) at room temperature under nitrogen in the dark (foil wrapped). Silver carbonate (3.70 g, 13.2 mmol) was added followed by iodomethane (6.2 mL, 99.4 mmol). The reaction mixture was allowed to stir at room temperature for 48 hours. The silver salts were removed by filtration through a pad of celite, washing with more chloroform and the filtrate concentrated in vacuo. The residue was purified by column chromatography to give the title compound as a white solid (3.14 g, 82% yield). MS (ES+) m/e=385. 1H NMR (CDCl3) δH 3.97 (3H, s), 5.23 (2H, s), 7.15 (1H, br s), 7.35-7.47 (5H, m), 8.00 (1H, s), 8.64 (1H, br s).

Aufarbeitung

  1. customThe silver salts were removed by filtration through a pad of celite
  2. washwashing with more chloroform
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-acd8390d30f74b01bb19a17820dd83ac
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338597B2

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