Phosphorus oxychloride → HCID 639412, Verbindung

HRID 1527671

Reaktionsgleichung

Reaktionsgleichung von HRID 1527671
CN([CH:9]=[O:10])C1C=CC=CC=1.O=P(Cl)(Cl)Cl.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[C:19]=1[O:28][CH3:29]>C(Cl)Cl.CCOC(C)=O>[CH3:16][O:17][C:18]1[C:19]([O:28][CH3:29])=[C:20]([O:26][CH3:27])[C:21]([O:24][CH3:25])=[CH:22][C:23]=1[CH:9]=[O:10]

Komponenten

6

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 66737N-MethylformanilideHCID 6077731,2,3,4-Tetramethoxybenzene

Produkt 1

HCID 639412HCID 639412, VerbindungAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Following the procedure by Syper et al.,19 N-methylformanilide (1.0 mL, 8.1 mmol) was added to a flame dried 10 mL round bottom flask under argon and a drying tube. POCl3 (1.0 mL, 11 mmol) was added at room temperature and the Argon line was removed. After 5 minutes 18 (1.067 g, 5.38 mmol) was dissolved in CH2Cl2 (2.0 mL) and added at room temperature. The reaction was stirred at room temperature under a drying tube for 48 hrs and monitored by 1H NMR. When complete the reaction was diluted with EtOAc, washed with saturated brine, dried over MgSO4, filtered, and condensed. The resulting product was separated from remaining N-methylformanilide using flash chromatography (1:4 Et2O:hexanes) to provide 19 (1.141 g, 5.04 mmol, 94%) as a colorless oil.

Aufarbeitung

  1. additionwas added to a flame
  2. customdried 10 mL round bottom flask under argon
  3. customthe Argon line was removed
  4. additionadded at room temperature
  5. washwashed with saturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customcondensed
  9. customThe resulting product was separated

Quellen und Nachweise

ORD-Eintrag
ord-c2c45e8f3a8348619eda0bf1daeb2587
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09089605B2

Verknüpfte Notizen

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