Diphosgene → HCID 59699561, Verbindung

HRID 901237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 901237
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[CH3:9][O:10][C:11]1[CH:27]=[CH:26][C:14]([CH2:15][NH:16][C:17]2[N:25]=[CH:24][CH:23]=[CH:22][C:18]=2[C:19]([OH:21])=[O:20])=[CH:13][CH:12]=1>O1CCOCC1>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[C:17]3[N:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19](=[O:21])[O:20][C:2]2=[O:3])=[CH:26][CH:27]=1

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 23856703HCID 23856703, Verbindung

Produkt 1

HCID 59699561HCID 59699561, VerbindungAusbeute 67,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Trichloromethyl chloroformate (3.36 mL, 27.8 mmol) was added slowly to a suspension of 2-(4-methoxy-benzylamino)-nicotinic acid (11) (6 g, 23.23 mmol) in dioxane and refluxed for 18 h under nitrogen atmosphere. The solution was cooled and the solvent was removed under vacuum. The residue was dissolved in dichloromethane and washed by saturated NaHCO3 solution. The organic phase was dried over Na2SO4 and evaporated to yield a residue. The residue was recrystallized by ether to yield 4.47 g (67%) of 1-(4-methoxy-benzyl)-1H-pyrido[2,3-d][1,3]oxazine-2,4-dione (12) as white solids. MP: 160° C.; 1H-NMR (DMSO-d6): δ 3.71 (s, 1H), 5.27 (s, 2H), 6.85 (d, J=7.0 Hz, 2H), 7.33 (m, 3H), 8.40 (dd, J=1.5, 7.5 Hz, 1H), 8.75 (dd, J=1.5, 7.5 Hz, 1H); EIMS: 286 (M+23).

Aufarbeitung

  1. temperaturerefluxed for 18 h under nitrogen atmosphere
  2. temperatureThe solution was cooled
  3. customthe solvent was removed under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed by saturated NaHCO3 solution
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customevaporated
  8. customto yield a residue
  9. customThe residue was recrystallized by ether

Quellen und Nachweise

ORD-Eintrag
ord-24b772d54e4f4305bbc1187dd5c7df86
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361760B2

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