Tributylphosphine → HCID 66764153, Verbindung

HRID 921999

Reaktionsgleichung

Reaktionsgleichung von HRID 921999
[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].[CH2:16]([P:20]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>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][P+:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:8]=1)(=[O:15])[CH3:14]

Komponenten

4

Edukt 2

HCID 13831TributylphosphineHCID 132776644-Acetamidophenyl chloroacetate

Produkt 1

HCID 66764153HCID 66764153, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-Acetamidophenyl 2-chloroacetate [2] (1.138 g, 5 mmol) and tributylphosphine (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 [6]. The crude product was crystallized twice from acetonitrile to give pure [6] in 65% yield. Identity and purity was confirmed via 1H and 13C NMR. The desired compound is isolated as colourless needles. 1H-NMR (300 MHz, d6-DMSO) δ(ppm)=10.49 (s, 1H), 7.71 (d, J=8.95 Hz, 2H), 7.12 (d, J=8.95 Hz, 2H), 4.18 (d, J=14.33, 2H), 2.41 (m, 3H), 2.06 (s, 3H), 1.55 (m, 6H), 1.41 (m, 6H), 0.91 (t, J=7.17). 31P-NMR (121.5 MHz, d6-DMSO) δ(ppm)=34.8. 13C-NMR (75 MHz, d6-DMSO) δ(ppm)=168.4, 164.7, 144.8, 137.8, 121.4, 119.9, 25.8 (d, J=47.9 Hz), 23.9, 23.3 (d, J=16.77 Hz), 22.6 (d, J=4.43 Hz), 18.2 (d, J=47.7 Hz), 13.2. mp 199° C. (dec), T5%onset 197° 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-3b86c66b24b64d1b8e6328e38ca4601f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278134B2

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