Vinylene carbonate → HCID 90110583, Verbindung

HRID 1508861

Reaktionsgleichung

Reaktionsgleichung von HRID 1508861
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].O1[CH:18]=[CH:17]OC1=O.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[O:12][CH:17]=[CH:18][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 3

HCID 13385Vinylene carbonateHCID 2336132-(4-Nitrophenyl)acetamideHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Produkt 1

HCID 90110583HCID 90110583, VerbindungAusbeute 25 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 2-(4-nitrophenyl)acetamide (1.0 g, 5.55 mmol), 1,3-dioxol-2-one (0.955 g, 11.10 mmol), and Eaton's Reagent (9.9 g, 34.97 mmol) was heated to 100° C. overnight under a nitrogen atmosphere. After this time, the reaction was cooled, diluted with ice water, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.250 g, 25%). MW=204.18. 1H NMR (DMSO-d6, 500 MHz) δ 8.26-8.18 (m, 2H), 8.05 (d, J=0.8 Hz, 1H), 7.57 (d, J=8.8 Hz, 2H), 7.16 (s, 1H), 4.34 (s, 2H); APCI MS m/z 205 [M+H]+.

Aufarbeitung

  1. temperatureAfter this time, the reaction was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Quellen und Nachweise

ORD-Eintrag
ord-0cd4594167a24100aa1fe8653a3acc07
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221843B2

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