Pyridine → 1-(2-(4-Acetamidophenoxy)-2-oxoethyl)pyridinium chloride

HRID 921998

Reaktionsgleichung

Reaktionsgleichung von HRID 921998
[Cl:1][CH2:2][C:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:4].[N:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(OCC)(=O)C>[Cl-:1].[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][C:3](=[O:4])[CH2:2][N+:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

Komponenten

4

Edukt 2

HCID 1049PyridineHCID 132776644-Acetamidophenyl chloroacetate

Produkt 1

HCID 866623411-(2-(4-Acetamidophenoxy)-2-oxoethyl)pyridinium chlorideAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Acetamidophenyl 2-chloroacetate [2] (1.138 g, 5 mmol) and pyridine (0.475 g, 6 mmol) were suspended in 50 ml of anhydrous ethyl acetate and refluxed for 48 hrs. After cooling to room temperature the white precipitate was filtered, washed with ethylacetate and diethylether and dried under reduced pressure to give [5] in 97% yield. The product was pure according to 1H NMR and was directly subjected to the next step without further purification. The desired compound is isolated as a colourless powder. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=10.31 (s, 1H), 9.27 (d, J=6.5 Hz, 2H), 8.76 (t, 7.9 Hz, 1H), 8.29 (t, 7.2 Hz, 2H), 7.71 (d, J=9.7 Hz, 2H), 7.11 (d, J=9.7 Hz, 2H), 4.69 (s, 2H), 2.08 (s, 3H). mp 199° C. (dec), T5%onset 198° C.

Aufarbeitung

  1. temperaturerefluxed for 48 hrs
  2. filtrationwas filtered
  3. washwashed with ethylacetate and diethylether
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-80e450c50c8f441480a2e0140187d156
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278134B2

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